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DOI: 10.1055/a-1757-2680
Forging C–C Bonds through Intramolecular Oxidative Coupling of Organoborates – An Overview
The Ludwig-Maximilians Universität and the Deutsche Forschungsgemeinschaft are kindly acknowledged for financial support (LMU Excellence and DI 2227/4-1).
Abstract
C–C bond formation has challenged the community of synthetic organic chemists for decades. Organoboron derivatives represent a mild and functional-group-tolerant class of reagents that can be handled without the need for inert conditions, making them suitable scaffolds for the development of methods that increase the sustainability of current processes for coupling reactions. This short review summarizes the different approaches that have been developed to enable C–C bond formation through intramolecular rearrangements of organoborate species.
1 Introduction
2 Oxidative Coupling with Chemical Oxidants
3 Electrocoupling of Tetraorganoborates
4 Photocoupling of Tetraorganoborates
# 1
Introduction
In contrast to classical organometallic reagents, organoboron derivatives present an advantageous stability towards moisture and ambient conditions, as well as a broad tolerance spectrum towards functional groups. This makes them suitable candidates for cross-coupling reactions – as popularized by Suzuki in the 1970s – in which boronic acids or esters are employed,[1] but also in plenty of other useful transformations and rearrangements. Organoboron reagents are commercially available or can be easily accessed by transmetalation,[2] hydroboration,[3] decarboxylative strategies,[4] C–H borylation,[5] or Miyaura borylation from organic halides.[6]
In the field of olefination reactions, among the different strategies that allow for the creation of carbon double bonds or for their introduction onto target molecules, Wittig’s outstanding work from 1954 is most popular.[7] In addition to several more contributions by others in following decades,[8] the Zweifel olefination represents a powerful and oftentimes overlooked method for the stereoselective formation of alkenes.[9] Zweifel olefinations were recently surveyed by the group of Aggarwal[10] and will therefore only be briefly summarized in this mini-review.
In the original transformation (Scheme [1]), an alkenyl group present on a tetraorganoborate 1 reacts with iodine towards the formation of an intermediate iodonium species 2, positioning thereby an electrophilic carbon α to the boron atom. This triggers a 1,2-metallate rearrangement of an adjacent ligand, leading to the 1,2-iodoboron 3, which undergoes an anti-periplanar β-elimination upon addition of a base.
The transformation is stereospecific, so that initial (E)-alkene 1 lead to (Z)-olefins 4 and vice versa. Moreover, it was later shown that replacing iodine with cyanogen bromide allows for a stereoselectivity switch through a syn-coplanar elimination.[11]
Zweifel olefination has been widely employed as a versatile strategic synthetic tool in many total syntheses of natural compounds such as bombykol,[12] (+)-faranal,[13] (–)-stemaphylline,[14] [5]-ladderanoic acid,[15] solaneoclepin A,[16] debromohamigeran E,[17] tatanan A,[18] (+)-scyphostatin,[19] herboxidiene,[20] or (–)-filiformin.[21]
Organomagnesium and organolithium reagents are traditionally employed for the formation of the organoboron species 1. The group of Aggarwal demonstrated that, while organolithium led quantitatively to bis-organoborinates (6) in the presence of organoboron pinacol esters (5), four equivalents of the corresponding organomagnesium reagents are needed to fully transform 5 into an organoborate. Alternatively, the amount of organomagnesium reagents could be decreased through addition of DMSO, towards the formation of 6.[22] In summary, organomagnesium reagents possess an advantageous tolerance towards functional groups but needs either a solvent system switch or to be applied in a large excess, and organolithium reagents possess an adequate reactivity towards organoboron species but prove less tolerant in the presence of sensitive functionalities. Our group recently introduced organocerium reagents to cope with disadvantages of both organo-lithium and -magnesium species. Tributylcerium allowed for efficient halogen–cerium exchanges on aryl- and alkenyl-halides, and the resulting organocerium reagents were successfully engaged in Zweifel olefinations.[23] Gratifyingly, all the organometallics underwent stereospecific transformations, as shown in Scheme [2] (7a–c).
In addition, the group of Aggarwal described a stereodivergent Zweifel olefination using selenides to promote a syn-elimination after oxidation.[24]
Transposing the concept of Zweifel olefination to C–C bond formation involving aryl groups would imply their dearomatization, in order to allow the key 1,2-metallate rearrangement step to proceed. There are therefore few activated aromatic systems, in which the dearomatization barrier is rendered accessible, that illustrate such strategy. Aggarwal and co-workers demonstrated this possibility on different systems that are prone to halogenations such as electron-rich furanyl and thiophenylborinates (8; Scheme [3]),[25] and aryls possessing a TMS-acetylene in the para-position (11). Electrophilic bromination of the latter promotes the 1,2-metallate rearrangement that gives the stabilized allene intermediate 13, further undergoing a remote elimination to form 12.[26] Another possibility relies on the use of 4-pyridinylborinates 14. The 1,2-metallate rearrangement occurs upon formation of the acylpyridinium 16, that then furnishes 15 after an oxidation/elimination sequence.[27] Chiral boronic esters were employed, resulting in stereospecific rearrangements in all cases (100% es). However, these strategies were only exemplified on specific substrates, with reachable dearomatization barriers, consequently limiting the scope of the transformation.
# 2
Oxidative Coupling with Chemical Oxidants
In 1971, Halpern showed that the use of stoichiometric amounts of hexachloroiridate enables the formation of biphenyl from sodium tetraphenylborate.[28] Although no mechanism was proposed for this rearrangement, it can easily be envisioned that negatively charged species such as Ph4B– are prone to oxidation on a phenyl position, promoting therefore a 1,2-metallate-type rearrangement of a second phenyl moiety (see mechanistic considerations below). Tetraarylborates (TABs 17, Scheme [4]) were later used by Hirao and co-workers under oxidative conditions with a Ph2SiCl2/O2 system.[29]
Whereas most of the compounds resulted from homocoupling reactions using symmetrical borates, few examples of heterocouplings were showcased (e.g., 18c, 67%). The main limitation in product diversity generally stems from the preparation of their starting borates. As a matter of fact, traditional methods rely on the addition of an organometallic reagent to expensive and oxygen-sensitive triarylboranes.[30]
The same group later illustrated the formation of biaryl compounds in similar systems using a different oxidation system based on a combination of VO(OEt)Cl2 and oxygen (Scheme [5]).[31] Reasonable yields were obtained from unsymmetrical borates, for cases in which the latter were accessed from triarylborane through addition of electron-rich aryls. When an electron-poor aryl was added (18c), a lower yield was obtained (10%). This difference in selectivity can be explained by the greater ability of electron-rich aryl moieties to undergo oxidation in comparison with electron-poor aryl moieties.
The same oxidation system (VO(OEt)Cl2/O2) was employed in alkynylation reactions of aryls, starting from mono-alkynylborates 19 (Scheme [6]),[32] providing an elegant alternative to classical methods for the construction of internal alkynes that include well-established Corey–Fuchs reactions,[33] Seyferth–Gilbert homologations,[34] Fritsch–Buttenberg–Wiechell rearrangements,[35] Pd-catalyzed Sonogashira couplings,[36] or simple 1,2-eliminations.[37] Importantly, the group of Lei recently reported elegant Pd-catalyzed cross-coupling reactions of alkynylstannanes or terminal alkynes towards disubstituted acetylenes.[38]
The strategy of Hirao allowed for the selective formation of disubstituted alkynes 20a–d in moderate to good yields (up to 79%). It is interesting to note that only one alkynyl moiety is present on the starting salt 19 (in contrast with the electrochemical oxidation shown in Scheme [15]), pointing out the preference of the chemical oxidant for the triple bond over aryl groups.
Most recently, the group of Studer exploited the potential of Bobbitt’s salt (BoS) to promote the oxidation of unsymmetrical TABs. Interestingly, they reported that electron-deficient aryl systems such as 3,5-bis(trifluoromethyl)phenyl groups do not undergo C–C bond formation with other aryl groups, and could therefore be used as dummy ligands in heterocoupling reactions (Scheme [7]). Two sets of conditions were applied, employing either stoichiometric or catalytic amounts of Bobbitt’s salt, providing a range of biaryl derivatives (22a–c) in moderate to good yields. The catalytic oxidation process was rendered possible through the introduction of additives such as NaNO2 and H2SO4 in the presence of oxygen.[39a]
In 2019, the group of Nitschke applied a macromolecular catalyst that they developed for the oxidative homocoupling of TABs (23, Scheme [8]) in the presence of TCBQ (tetrachloro-1,4-benzoquinone) as chemical oxidant.[39b]
# 3
Electrocoupling of Tetraorganoborates
The field of electrochemistry has recently witnessed a growing interest among the community of organic chemists due to its wide range of applications.[40] In 1959, Geske discovered that tetraphenylborate undergoes formation of biphenyl 25a under electrochemical oxidation (Scheme [9]).[41] Recently, Waldvogel and co-workers built on this first observation, demonstrating the electrochemical instability of highly fluorinated tetraphenylborates towards homocoupling products (e.g., 25b), providing insights on the intramolecular nature of the rearrangement.[42]
The main issue for the formation of heterobiaryl structures stems from the availability of starting unsymmetrical borate salts. In 2020, the group of Didier proposed a simple method to access their structure, through triple ligand exchange, using organo-magnesium or -zinc reagents onto commercial or easily accessible functionalized potassium trifluoroborates 26 (see Scheme [11]). Borate salts 27 were primarily designed following the logic that the most electron-rich aryl group in the system should undergo favorable oxidation over other – electron-poorer – aryl groups.[43] Both theoretical calculations at quantum chemical levels and cyclic voltammetry measurements supported this hypothesis. Scheme [10] shows that oxidation potentials increase with decreasing electron-density on aryl groups. Mulliken charge calculations also placed the loss of electrons resulting from an oxidation process on the most electron-rich moiety (p-MeOC6H4), keeping the electronic integrity of electron-poor aryls (p-FC6H4).
After oxidation, one of the three remaining aryl moieties can be engaged in C–C bond formation to obtain heterobiaryl derivatives selectively and avoid homocoupling products.
Although these unsymmetrical borate salts 27 could be isolated, the authors described a simpler sequence in which the salts were engaged in the electrocoupling reactions without prior purification (Scheme [11]).[43] Given the high tolerance of organoborates, RVC (reticulated vitreous carbon) electrodes were used in acetonitrile in an open-to-air setup. The scope of the reaction was widely explored with various aryl and heteroaryl moieties (28a–c), including natural scaffolds, and showed exceptional selectivity.
The mechanism of the C–C bond formation was evaluated, considering both experimental and theoretical data. Crossover experiments were conducted to assess the intra- or intermolecular nature of the coupling (Scheme [12]).[43] Two borate salts 29 and 30 were engaged under electrochemical oxidative conditions, resulting in the major formation of heterocoupling products 31a and 31b. Homocoupling products 32a and 32b were only observed in trace amounts. This observation supports an intramolecular mechanism, as products 33a–e, coming from intermolecular rearrangements, were not formed during the reaction.
The group of Jagau further investigated the mechanism through theoretical calculations, providing insights into the key C–C bond-formation process.[44] Their results seem to point towards a π-bond addition onto the dearomatized aryl structure ([A]→[C]→[B]) rather than a direct σ-bond cleavage ([A]→[B], Scheme [13]).
Potentiostatic experiments were finally performed to determine whether the rearrangement follows a one- or two-electron process. Setting up the voltage to 1.6 V (vs. SCE) gave the same results as those under galvanostatic conditions, supporting a one-electron mechanism. This hypothesis was also advocated by the observation of a 57% GC-yield after one-electron equivalent.
Didier’s group later reported a similar strategy employing alkenyl-triarylborates as intermediates.[45] Given that alkenyl electrons are more accessible than aryl electrons, the oxidation was expected to proceed on the double bond rather than on the aromatic system, as it would additionally lead to dearomatization. While classical Zweifel olefinations lead to (E)- or (Z)-alkenes stereospecifically, depending on the original configuration of the starting bis-organoborinates, a procedure based on intermediate formation of an alkyl radical cation should undergo stereoconvergence towards the thermodynamic product. This assumption was confirmed by engaging (E)- and (Z)-alkenylborates 34, which gave products 36a–d of (E)-configuration preferentially (Scheme [14]).
In contrast to alkenyl groups, the oxidation of alkynyl moieties is not favored over aryls. Electrochemical alkynylation procedures can therefore only be chemoselective with one aryl on the borate (37), in the presence of three alkynyl groups. This strategy was illustrated on a large range of substrates (Scheme [15]), although corresponding alkynes 38 were generally obtained in lower yields than alkenes and biaryl derivatives.[46]
# 4
Photocoupling of Tetraorganoborates
Photocatalysis has been a rapidly expanding domain in organic synthesis over the last decades. However, reports that concentrate on aryl–aryl bond formation are scarce.[47] Doty was the first to report the photochemical oxidation of tetraphenylborate towards biphenyl under UV irradiation in the presence of Rose Bengal, in 1971. The reaction takes place in the presence of oxygen, and the singlet state was assumed to be the oxidizing species in the reaction.[48] In 2021, Didier and co-workers illustrated a photocatalytic version of the electrocoupling reaction, using acridinium species as photocatalysts under blue-light irradiation.[49] A wide variety of substrates 27 were used to demonstrate the applicability of the strategy, including halogenated derivatives (Scheme [16]). It is important to note that polyhalogenated substrates usually undergo formation of undesired products under Pd-catalyzed conditions, including homocoupling products and polymers. However, the rearrangement of borates occurs specifically between the carbons directly attached to the boron atom, thereby allowing for a high functional group tolerance (39a–d).
To summarize, significant progress has been made towards catalyst- and/or metal-free cross-coupling reactions, relying on the use of chemical oxidants, electrochemistry or photocatalysis. These methods provide reliable alternatives to the use of expensive and/or toxic transition metals for essential C–C bond-forming reactions. However, although big steps have been taken towards more sustainable strategies, atom-economy remains an issue, as two organic moieties are inevitably lost in the process. It is therefore necessary for new methods to be developed for the synthesis and evaluation of coupling reactions of boron species that will allow for greener transformations.
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Conflict of Interest
The authors declare no conflict of interest.
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References
- 1a Miyaura N, Suzuki A. J. Chem. Soc., Chem. Commun. 1979; 866
- 1b Miyaura N, Yamada K, Suzuki A. Tetrahedron Lett. 1979; 20: 3437
- 1c Johansson Seechurn CC. C, Kitching MO, Colacot TJ, Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062
- 2a Li W, Nelson DP, Jensen MS, Hoerrner RS, Cai D, Larsen RD, Reider PJ. J. Org. Chem. 2002; 67: 5394
- 2b Oberli MA, Buchwald SL. Org. Lett. 2012; 14: 4606
- 2c Billingsley KL, Buchwald SL. Angew. Chem. Int. Ed. 2008; 47: 4695
- 2d Haag BA, Sämann C, Jana A, Knochel P. Angew. Chem. Int. Ed. 2011; 50: 7290
- 2e Baumann AN, Eisold M, Music A, Didier D. Synthesis 2018; 50: 3149
- 3 Brown HC. Tetrahedron 1961; 12: 117
- 4a Wang J, Shang M, Lundberg H, Feu KS, Hecker SJ, Qin T, Blackmond DG, Baran PS. ACS Catal. 2018; 8: 9537
- 4b Candish L, Teders M, Glorius F. J. Am. Chem. Soc. 2017; 139: 7440
- 4c Li C, Wang J, Barton LM, Yu S, Tian M, Peters DS, Kumar M, Yu AW, Johnson KA, Chatterjee AK, Yan M, Baran PS. Science 2017; 356: 1045
- 4d Fawcett A, Pradeilles J, Wang Y, Matsuga T, Myers EL, Aggarwal VK. Science 2017; 357: 283
- 5a Larsen MA, Hartwig JF. J. Am. Chem. Soc. 2014; 136: 4287
- 5b Xu L, Wang G, Zhang S, Wang H, Liu L, Jiao J, Li P. Tetrahedron 2017; 73: 7123 ; and references therein
- 6a Ishiyama T, Murata M, Miyaura N. J. Org. Chem. 1995; 60: 7508
- 6b Barroso S, Joksch M, Puylaert P, Tin S, Bell SJ, Donnellan L, Duguid S, Muir C, Zhao P, Farina V, Tran DN, de Vries JG. J. Org. Chem. 2021; 86: 103
- 7a Wittig G, Schöllkopf U. Chem. Ber. 1954; 87: 1318
- 7b Wittig G, Haag W. Chem. Ber. 1955; 88: 1654
- 7c Maryanoff BE, Reitz AB. Chem. Rev. 1989; 89: 863
- 7d Hoffmann RW. Angew. Chem. Int. Ed. 2001; 40: 1411
- 8a Peterson DJ. J. Org. Chem. 1968; 33: 780
- 8b Tebbe FN, Parshall GW, Reddy GS. J. Am. Chem. Soc. 1978; 100: 3611
- 8c Horner L, Hoffmann H, Wippel HG. Chem. Ber. 1958; 91: 61
- 8d Wadsworth WS, Emmons WD. J. Am. Chem. Soc. 1961; 83: 1733
- 8e Takai K, Nitta K, Utimoto K. J. Am. Chem. Soc. 1986; 108: 7408
- 8f McMurry JE, Fleming MP. J. Am. Chem. Soc. 1974; 96: 4708
- 8g Julia M, Paris Y.-M. Tetrahedron Lett. 1973; 14: 4833
- 9a Zweifel G, Arzoumanian H, Whitney CC. J. Am. Chem. Soc. 1967; 89: 3652
- 9b Zweifel G, Polston NL, Whitney CC. J. Am. Chem. Soc. 1968; 90: 6243
- 10 Armstrong RJ, Aggarwal VK. Synthesis 2017; 49: 3323
- 11a Zweifel G, Fisher RP, Snow JT, Whitney CC. J. Am. Chem. Soc. 1972; 94: 6560
- 11b Armstrong RJ, García-Ruiz C, Myers EL, Aggarwal VK. Angew. Chem. Int. Ed. 2017; 56: 786
- 12 Negishi E, Lew G, Yoshida T. J. Chem. Soc., Chem. Commun. 1973; 874
- 13 Dutheuil G, Webster MP, Worthington PA, Aggarwal VK. Angew. Chem. Int. Ed. 2009; 48: 6317
- 14 Varela A, Garve LK. B, Leonori D, Aggarwal VK. Angew. Chem. Int. Ed. 2017; 56: 2127
- 15 Mercer JA. M, Cohen CM, Shuken SR, Wagner AM, Smith MW, Moss FR, Smith MD, Vahala R, Gonzalez Martinez A, Boxer SG, Burns NZ. J. Am. Chem. Soc. 2016; 138: 15845
- 16 Kleinnijenhuis RA, Timmer BJ. J, Lutteke G, Smits JM. M, de Gelder R, van Maarseveen JH, Hiemstra H. Chem. Eur. J. 2016; 22: 1266
- 17 Blaisdell TP, Morken JP. J. Am. Chem. Soc. 2015; 137: 8712
- 18 Noble A, Roesner S, Aggarwal VK. Angew. Chem. Int. Ed. 2016; 55: 15920
- 19 Xu S, Lee C.-T, Rao H, Negishi E. Adv. Synth. Catal. 2011; 353: 2981
- 20 Meng F, McGrath KP, Hoveyda AH. Nature 2014; 513: 367
- 21 Blair DJ, Fletcher CJ, Wheelhouse KM. P, Aggarwal VK. Angew. Chem. Int. Ed. 2014; 53: 5552
- 22 Armstrong RJ, Niwetmarin W, Aggarwal VK. Org. Lett. 2017; 19: 2762
- 23a Music A, Hoarau C, Hilgert N, Zischka F, Didier D. Angew. Chem. Int. Ed. 2019; 58: 1188
- 23b Music A, Didier D. Synlett 2019; 30: 1843
- 23c Music A, Baumann AN, Spieß P, Hilgert N, Köllen M, Didier D. Org. Lett. 2019; 21: 2189
- 24 Armstrong RJ, García-Ruiz C, Myers EL, Aggarwal VK. Angew. Chem. Int. Ed. 2017; 56: 786
- 25a Bonet A, Odachowski M, Leonori D, Essafi S, Aggarwal VK. Nat. Chem. 2014; 6: 584
- 25b Wang Y, Noble A, Sandford C, Aggarwal VK. Angew. Chem. Int. Ed. 2017; 56: 1810
- 25c Odachowski M, Bonet A, Essafi S, Conti-Ramsden P, Harvey JN, Leonori D, Aggarwal VK. J. Am. Chem. Soc. 2016; 138: 9521
- 26 Ganesh V, Odachowski M, Aggarwal VK. Angew. Chem. Int. Ed. 2017; 56: 9752
- 27 Llaveria J, Leonori D, Aggarwal VK. J. Am. Chem. Soc. 2015; 137: 10958
- 28 Abley P, Halpern J. J. Chem. Soc. D 1971; 1238
- 29 Sakurai H, Morimito C, Hirao T. Chem. Lett. 2001; 30: 1084
- 30 Brown HC, Racherla US. J. Org. Chem. 1986; 51: 427
- 31 Mizuno H, Sakurai H, Amaya T, Hirao T. Chem. Commun. 2006; 5042
- 32 Amaya T, Tsukamura Y, Hirao T. Adv. Synth. Catal. 2009; 351: 1025
- 33 Corey EJ, Fuchs PL. Tetrahedron Lett. 1972; 13: 3769
- 34a Seyferth D, Marmor RS, Hilbert P. J. Org. Chem. 1971; 36: 1379
- 34b Gilbert JC, Weerasooriya U. J. Org. Chem. 1982; 47: 1837
- 35 Jahnke E, Tykwinski RR. Chem. Commun. 2010; 46: 3235
- 36 Chinchilla R, Nájera C. Chem. Rev. 2007; 107: 874
- 37 Shaw R, Elagamy A, Althagafi I, Pratap R. Org. Biomol. Chem. 2020; 18: 3797
- 38a Zhao Y, Wang H, Hou X, Lei A, Zhang H, Zhu L. J. Am. Chem. Soc. 2006; 128: 15048
- 38b Chen M, Zheng X, Li W, He J, Lei A. J. Am. Chem. Soc. 2010; 132: 4101
- 39a Gerleve C, Studer A. Angew. Chem. Int. Ed. 2020; 59: 15468
- 39b Lu Z, Lavendomme R, Burghaus O, Nitschke R. Angew. Chem. Int. Ed. 2019; 58: 9073
- 40a Yan M, Kawamata Y, Baran PS. Chem. Rev. 2017; 117: 13230
- 40b Horn EJ, Rosen RR, Baran PS. ACS Cent. Sci. 2016; 2: 302
- 40c Yoshida J.-i, Shimizu A, Hayashi R. Chem. Rev. 2018; 118: 4702
- 40d Morofuji T, Shimizu A, Yoshida J.-i. J. Am. Chem. Soc. 2013; 135: 5000
- 40e Yoshida J.-i, Nishiwaki K. J. Chem. Soc., Dalton Trans. 1998; 2589
- 40f Elsler B, Schollmeyer D, Dyballa KM, Franke R, Waldvogel SR. Angew. Chem. Int. Ed. 2014; 53: 5210
- 40g Kirste A, Elsler B, Schnakenburg G, Waldvogel SR. J. Am. Chem. Soc. 2012; 134: 3571
- 40h Shono T, Hamaguchi H, Matsumura Y. J. Am. Chem. Soc. 1975; 97: 4264
- 40i Kärkäs MD. Chem. Soc. Rev. 2018; 47: 5786
- 41 Geske DH. J. Phys. Chem. Soc. 1975; 97: 4264
- 42 Beil SB, Möhle S, Enders P, Waldvogel SR. Chem. Commun. 2018; 54: 6128
- 43 Music A, Baumann AN, Spieß P, Plantefol A, Jagau TC, Didier D. J. Am. Chem. Soc. 2020; 142: 4341
- 44 Matz F, Music A, Didier D, Jagau TC. Electrochen. Sci. Adv. 2022; 2: e2100032
- 45 Baumann AN, Music A, Dechent J, Müller N, Jagau TC, Didier D. Chem. Eur. J. 2020; 26: 8382
- 46 Music A, Nuber CM, Lemke Y, Spieß P, Didier D. Org. Lett. 2021; 23: 4179
- 47a Kalyani D, McMurtrey KB, Neufeldt SR, Sanford MS. J. Am. Chem. Soc. 2011; 133: 18566
- 47b Zeng L, Liu T, He C, Shi D, Zhang F, Duan C. J. Am. Chem. Soc. 2016; 138: 3958
- 47c Hari DP, Schroll P, Kçnig B. J. Am. Chem. Soc. 2012; 134: 2958
- 47d Ghosh I, Ghosh T, Bardagi JI, Kçnig B. Science 2014; 346: 725
- 47e Meyer AU, Slanina T, Yao C.-J, Kçnig B. ACS Catal. 2016; 6: 369
- 48 Doty JC, Grisdale PJ, Evans TR, Williams JL. R. J. Organomet. Chem. 1971; 32: C35
- 49 Music A, Baumann AN, Boser F, Müller N, Matz F, Jagau TC, Didier D. Chem. Eur. J. 2021; 27: 4322
Corresponding Author
Publication History
Received: 11 January 2022
Accepted after revision: 01 February 2022
Accepted Manuscript online:
01 February 2022
Article published online:
06 April 2022
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-
References
- 1a Miyaura N, Suzuki A. J. Chem. Soc., Chem. Commun. 1979; 866
- 1b Miyaura N, Yamada K, Suzuki A. Tetrahedron Lett. 1979; 20: 3437
- 1c Johansson Seechurn CC. C, Kitching MO, Colacot TJ, Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062
- 2a Li W, Nelson DP, Jensen MS, Hoerrner RS, Cai D, Larsen RD, Reider PJ. J. Org. Chem. 2002; 67: 5394
- 2b Oberli MA, Buchwald SL. Org. Lett. 2012; 14: 4606
- 2c Billingsley KL, Buchwald SL. Angew. Chem. Int. Ed. 2008; 47: 4695
- 2d Haag BA, Sämann C, Jana A, Knochel P. Angew. Chem. Int. Ed. 2011; 50: 7290
- 2e Baumann AN, Eisold M, Music A, Didier D. Synthesis 2018; 50: 3149
- 3 Brown HC. Tetrahedron 1961; 12: 117
- 4a Wang J, Shang M, Lundberg H, Feu KS, Hecker SJ, Qin T, Blackmond DG, Baran PS. ACS Catal. 2018; 8: 9537
- 4b Candish L, Teders M, Glorius F. J. Am. Chem. Soc. 2017; 139: 7440
- 4c Li C, Wang J, Barton LM, Yu S, Tian M, Peters DS, Kumar M, Yu AW, Johnson KA, Chatterjee AK, Yan M, Baran PS. Science 2017; 356: 1045
- 4d Fawcett A, Pradeilles J, Wang Y, Matsuga T, Myers EL, Aggarwal VK. Science 2017; 357: 283
- 5a Larsen MA, Hartwig JF. J. Am. Chem. Soc. 2014; 136: 4287
- 5b Xu L, Wang G, Zhang S, Wang H, Liu L, Jiao J, Li P. Tetrahedron 2017; 73: 7123 ; and references therein
- 6a Ishiyama T, Murata M, Miyaura N. J. Org. Chem. 1995; 60: 7508
- 6b Barroso S, Joksch M, Puylaert P, Tin S, Bell SJ, Donnellan L, Duguid S, Muir C, Zhao P, Farina V, Tran DN, de Vries JG. J. Org. Chem. 2021; 86: 103
- 7a Wittig G, Schöllkopf U. Chem. Ber. 1954; 87: 1318
- 7b Wittig G, Haag W. Chem. Ber. 1955; 88: 1654
- 7c Maryanoff BE, Reitz AB. Chem. Rev. 1989; 89: 863
- 7d Hoffmann RW. Angew. Chem. Int. Ed. 2001; 40: 1411
- 8a Peterson DJ. J. Org. Chem. 1968; 33: 780
- 8b Tebbe FN, Parshall GW, Reddy GS. J. Am. Chem. Soc. 1978; 100: 3611
- 8c Horner L, Hoffmann H, Wippel HG. Chem. Ber. 1958; 91: 61
- 8d Wadsworth WS, Emmons WD. J. Am. Chem. Soc. 1961; 83: 1733
- 8e Takai K, Nitta K, Utimoto K. J. Am. Chem. Soc. 1986; 108: 7408
- 8f McMurry JE, Fleming MP. J. Am. Chem. Soc. 1974; 96: 4708
- 8g Julia M, Paris Y.-M. Tetrahedron Lett. 1973; 14: 4833
- 9a Zweifel G, Arzoumanian H, Whitney CC. J. Am. Chem. Soc. 1967; 89: 3652
- 9b Zweifel G, Polston NL, Whitney CC. J. Am. Chem. Soc. 1968; 90: 6243
- 10 Armstrong RJ, Aggarwal VK. Synthesis 2017; 49: 3323
- 11a Zweifel G, Fisher RP, Snow JT, Whitney CC. J. Am. Chem. Soc. 1972; 94: 6560
- 11b Armstrong RJ, García-Ruiz C, Myers EL, Aggarwal VK. Angew. Chem. Int. Ed. 2017; 56: 786
- 12 Negishi E, Lew G, Yoshida T. J. Chem. Soc., Chem. Commun. 1973; 874
- 13 Dutheuil G, Webster MP, Worthington PA, Aggarwal VK. Angew. Chem. Int. Ed. 2009; 48: 6317
- 14 Varela A, Garve LK. B, Leonori D, Aggarwal VK. Angew. Chem. Int. Ed. 2017; 56: 2127
- 15 Mercer JA. M, Cohen CM, Shuken SR, Wagner AM, Smith MW, Moss FR, Smith MD, Vahala R, Gonzalez Martinez A, Boxer SG, Burns NZ. J. Am. Chem. Soc. 2016; 138: 15845
- 16 Kleinnijenhuis RA, Timmer BJ. J, Lutteke G, Smits JM. M, de Gelder R, van Maarseveen JH, Hiemstra H. Chem. Eur. J. 2016; 22: 1266
- 17 Blaisdell TP, Morken JP. J. Am. Chem. Soc. 2015; 137: 8712
- 18 Noble A, Roesner S, Aggarwal VK. Angew. Chem. Int. Ed. 2016; 55: 15920
- 19 Xu S, Lee C.-T, Rao H, Negishi E. Adv. Synth. Catal. 2011; 353: 2981
- 20 Meng F, McGrath KP, Hoveyda AH. Nature 2014; 513: 367
- 21 Blair DJ, Fletcher CJ, Wheelhouse KM. P, Aggarwal VK. Angew. Chem. Int. Ed. 2014; 53: 5552
- 22 Armstrong RJ, Niwetmarin W, Aggarwal VK. Org. Lett. 2017; 19: 2762
- 23a Music A, Hoarau C, Hilgert N, Zischka F, Didier D. Angew. Chem. Int. Ed. 2019; 58: 1188
- 23b Music A, Didier D. Synlett 2019; 30: 1843
- 23c Music A, Baumann AN, Spieß P, Hilgert N, Köllen M, Didier D. Org. Lett. 2019; 21: 2189
- 24 Armstrong RJ, García-Ruiz C, Myers EL, Aggarwal VK. Angew. Chem. Int. Ed. 2017; 56: 786
- 25a Bonet A, Odachowski M, Leonori D, Essafi S, Aggarwal VK. Nat. Chem. 2014; 6: 584
- 25b Wang Y, Noble A, Sandford C, Aggarwal VK. Angew. Chem. Int. Ed. 2017; 56: 1810
- 25c Odachowski M, Bonet A, Essafi S, Conti-Ramsden P, Harvey JN, Leonori D, Aggarwal VK. J. Am. Chem. Soc. 2016; 138: 9521
- 26 Ganesh V, Odachowski M, Aggarwal VK. Angew. Chem. Int. Ed. 2017; 56: 9752
- 27 Llaveria J, Leonori D, Aggarwal VK. J. Am. Chem. Soc. 2015; 137: 10958
- 28 Abley P, Halpern J. J. Chem. Soc. D 1971; 1238
- 29 Sakurai H, Morimito C, Hirao T. Chem. Lett. 2001; 30: 1084
- 30 Brown HC, Racherla US. J. Org. Chem. 1986; 51: 427
- 31 Mizuno H, Sakurai H, Amaya T, Hirao T. Chem. Commun. 2006; 5042
- 32 Amaya T, Tsukamura Y, Hirao T. Adv. Synth. Catal. 2009; 351: 1025
- 33 Corey EJ, Fuchs PL. Tetrahedron Lett. 1972; 13: 3769
- 34a Seyferth D, Marmor RS, Hilbert P. J. Org. Chem. 1971; 36: 1379
- 34b Gilbert JC, Weerasooriya U. J. Org. Chem. 1982; 47: 1837
- 35 Jahnke E, Tykwinski RR. Chem. Commun. 2010; 46: 3235
- 36 Chinchilla R, Nájera C. Chem. Rev. 2007; 107: 874
- 37 Shaw R, Elagamy A, Althagafi I, Pratap R. Org. Biomol. Chem. 2020; 18: 3797
- 38a Zhao Y, Wang H, Hou X, Lei A, Zhang H, Zhu L. J. Am. Chem. Soc. 2006; 128: 15048
- 38b Chen M, Zheng X, Li W, He J, Lei A. J. Am. Chem. Soc. 2010; 132: 4101
- 39a Gerleve C, Studer A. Angew. Chem. Int. Ed. 2020; 59: 15468
- 39b Lu Z, Lavendomme R, Burghaus O, Nitschke R. Angew. Chem. Int. Ed. 2019; 58: 9073
- 40a Yan M, Kawamata Y, Baran PS. Chem. Rev. 2017; 117: 13230
- 40b Horn EJ, Rosen RR, Baran PS. ACS Cent. Sci. 2016; 2: 302
- 40c Yoshida J.-i, Shimizu A, Hayashi R. Chem. Rev. 2018; 118: 4702
- 40d Morofuji T, Shimizu A, Yoshida J.-i. J. Am. Chem. Soc. 2013; 135: 5000
- 40e Yoshida J.-i, Nishiwaki K. J. Chem. Soc., Dalton Trans. 1998; 2589
- 40f Elsler B, Schollmeyer D, Dyballa KM, Franke R, Waldvogel SR. Angew. Chem. Int. Ed. 2014; 53: 5210
- 40g Kirste A, Elsler B, Schnakenburg G, Waldvogel SR. J. Am. Chem. Soc. 2012; 134: 3571
- 40h Shono T, Hamaguchi H, Matsumura Y. J. Am. Chem. Soc. 1975; 97: 4264
- 40i Kärkäs MD. Chem. Soc. Rev. 2018; 47: 5786
- 41 Geske DH. J. Phys. Chem. Soc. 1975; 97: 4264
- 42 Beil SB, Möhle S, Enders P, Waldvogel SR. Chem. Commun. 2018; 54: 6128
- 43 Music A, Baumann AN, Spieß P, Plantefol A, Jagau TC, Didier D. J. Am. Chem. Soc. 2020; 142: 4341
- 44 Matz F, Music A, Didier D, Jagau TC. Electrochen. Sci. Adv. 2022; 2: e2100032
- 45 Baumann AN, Music A, Dechent J, Müller N, Jagau TC, Didier D. Chem. Eur. J. 2020; 26: 8382
- 46 Music A, Nuber CM, Lemke Y, Spieß P, Didier D. Org. Lett. 2021; 23: 4179
- 47a Kalyani D, McMurtrey KB, Neufeldt SR, Sanford MS. J. Am. Chem. Soc. 2011; 133: 18566
- 47b Zeng L, Liu T, He C, Shi D, Zhang F, Duan C. J. Am. Chem. Soc. 2016; 138: 3958
- 47c Hari DP, Schroll P, Kçnig B. J. Am. Chem. Soc. 2012; 134: 2958
- 47d Ghosh I, Ghosh T, Bardagi JI, Kçnig B. Science 2014; 346: 725
- 47e Meyer AU, Slanina T, Yao C.-J, Kçnig B. ACS Catal. 2016; 6: 369
- 48 Doty JC, Grisdale PJ, Evans TR, Williams JL. R. J. Organomet. Chem. 1971; 32: C35
- 49 Music A, Baumann AN, Boser F, Müller N, Matz F, Jagau TC, Didier D. Chem. Eur. J. 2021; 27: 4322