Subscribe to RSS
DOI: 10.1055/a-2039-9942
Visible-Light Photocatalytic Barbier-Type Reaction of Aziridines and Azetidines with Nonactivated Aldehydes
Financial support was provided by the National Natural Science Foundation of China (22101192), Sichuan Normal University (024-341914001), the Opening Foundation of the Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province (2021KFKT03), and the Fundamental Research Funds for the Central Universities.
Dedicated to Prof. Dr. Masahiro Murakami for his great contributions to science.
Abstract
Barbier-type reactions are a classic group of reactions for carbon–carbon bond formation; however, their common use of stoichiometric metals restricts their widespread application. Considering the ready availability and diversity of cyclic amines, we report a visible-light photocatalytic Barbier-type reaction of aziridines and azetidines with nonactivated aldehydes. A series of important γ- and δ-amino alcohols were synthesized in the presence of amines as electron donors. Moreover, this transition-metal-free protocol displays mild reaction conditions, broad functional-group tolerance, and a wide substrate scope. Mechanistic investigations indicated that carbon radicals and carbanions might be generated as key intermediates.
#
C–C bond-formation processes are an essential class of reactions for the construction of the skeletons of organic compounds.[1] Many classic reactions have been developed to form C–C bonds, among which Barbier-type reactions are among the most important and convenient. In these reactions, organometallic intermediates undergo nucleophilic attack on carbonyl compounds.[2] Although the reactions were discovered more than a century ago, they still have many uses in modern synthetic organic chemistry. In conventional Barbier-type reactions, a metal reductant such as Mg, Zn, Sn, or In is typically required to generate an organometallic intermediate by the reduction of an organic (pseudo)halide (Scheme [1]A). However, the use of metal reductants hampers the widespread application of this type of reaction due to the harsh conditions required, the formation of metal residues, and safety issues. It is therefore highly desirable to develop new strategies to address these issues. Recently, visible-light photocatalysis has emerged as a practical, mild, and powerful tool for generating carbanion equivalents for use in C–C bond formations.[3] Photocatalytic Barbier-type reactions of carbonyl compounds have been developed to deliver valuable alcohols in a green and sustainable manner (Scheme [1]B).[4] Notably, the use of organic amines to replace active metals as reducing agents improves the controllability of such reactions; however, the substrate scope and product diversity remain limited.
Cyclic amines, such as aziridines and azetidines, are readily available and are frequently found in a wide range of natural products and synthetic compounds.[5] Therefore, many methods are aimed at the diversification of cyclic amines to provide value-added molecules.[6] Ring-opening of aziridines and azetidines, which represents a valuable skeletal-diversification strategy, has attracted widespread attention.[7] The reductive ring-opening functionalization can be coupled with various electrophiles, which is an alternative to the conventional nucleophilic ring-opening process.[8] Although this strategy has not been well studied due to the essentially electron-rich properties of aziridines and azetidines, the reductive ring-opening functionalization of these compounds has been achieved by several methods, such as transition-metal catalysis with metal reductants.[9] However, the limited activation modes and the need for excess metal reductants have led to poor compatibility. Therefore, it is highly desirable to develop a simple, green, and sustainable strategy for realizing the general reductive ring-opening functionalization of aziridines and azetidines. Inspired by previous reports on the photocatalytic reductive ring-opening functionalization of aziridines and azetidines, and one example of a reductive coupling with an aldehyde,[10] we proposed that a successive-single-electron transfer (SSET)[3e] [h] reduction of aziridines or azetidines would generate carbanions that would undergo nucleophilic attack on alkyl aldehydes to give valuable γ- and δ-amino alcohols, which are widely used in medicinal and synthetic chemistry.[11] However, this hypothetical route involves several challenges: (1) aziridines and azetidines, with low reduction potentials, are difficult to reduce according to previous reports; (2) the reductive protonation and homocoupling of cyclic amines, as major side reactions, are highly competitive with the desired reductive functionalization; and (3) alkyl aldehydes could compete with aziridines or azetidines for reduction, giving alkyl alcohols and homocoupling byproducts.[12] Here, we report a visible-light photocatalytic Barbier-type reaction of aziridines and azetidines with nonactivated aldehydes through reductive cleavage of C–N bonds[13] (Scheme [1]C). A variety of important γ- and δ-amino alcohols were obtained in moderate to good yields.[14]
a Standard conditions. 1a (0.2 mmol), 2a (0.4 mmol), 3DPAFIPN (0.004 mmol), DIPEA (0.4 mmol), PivOK (0.2 mmol), DMAc (2.0 mL), 30 W blue LEDs, rt, 36 h.
b Isolated yields.
c Not detected.
d 2,4,5,6-Tetrakis(diphenylamino)isophthalonitrile.
Taking into consideration the fact that ring-opening of azetidines is more difficult than that of aziridines,[15] we decided to examine the coupling reaction of tert-butyl 2-biphenyl-4-ylazetidine-1-carboxylate (1a) with 3-phenylpropanal (2a) (Table [1]). After systematic screening of the reaction parameters, the desired product 3aa was obtained in 82% isolated yield by using 2 mol% of 2,4,6-tris(diphenylamino)-5-fluoroisophthalonitrile (3DPAFIPN) as the photocatalyst, N,N-diisopropylethylamine (DIPEA) as the reductant, PivOK as the base, and N,N-dimethylacetamide (DMA) as the solvent (Table [1], entry 1). Control experiments showed that light and the photocatalyst were indispensable for this transformation (entries 2 and 3), and that the reductant and base were important to increase the yield of 3aa (entries 4 and 5). Other photocatalysts, reductants, bases, and solvents were investigated, but gave lower yields of 3aa (entries 6–9). Notably, the reaction time could be shortened to 12 hours with little effect on the yield (Entry 10).
After establishing the optimal conditions, we turned our attention to evaluating the substrate scope of 2-arylazetidines with nonactivated aldehydes (Scheme [2]). Various alkyl aldehydes bearing short or long chains reacted well in this reaction, giving the desired products 3aa–ad in yields of 66–82%. Substituents in the β-position were compatible (3ae and 3af). The presence of additional substituents at the α-carbon (3ag–ai) did not affect the reaction, demonstrating its tolerance to steric hindrance. Some useful functional groups were tolerated in this system, such as ether (3ai) or alkenyl (3aj) groups. Notably, paraformaldehyde also reacted to provide the desired product 3ak in 28% yield. In addition, various 2-arylazetidines also worked well, including phenyl- (3bb), m-methoxyphenyl- (3cb), m-phenoxyphenyl- (3dc) and naphthyl-substituted (3ec) azetidines.
To further explore the potential of this reaction, we then investigated the scope of the 2-arylaziridines with alkyl aldehydes (Scheme [3]). To our delight, the reaction proceeded with two sterically hindered aldehydes (5af and 5ag). Moreover, 2-arylaziridines with either electron-donating groups (5ba and 5ca) or electron-withdrawing group (5da) at the para-position of the aryl ring were compatible, delivering the corresponding γ-amino alcohol products in moderate to good yields. Moreover, meta- and ortho-substituted 2-arylaziridines also reacted smoothly (5ea and 5fa). Importantly, a highly challenging 2-arylaziridine bearing a tertiary C–N bond was amenable to this transformation to give product 5ga in a 67% yield.
To gain insights into the reaction mechanism, we conducted two control experiments (Scheme [4]). When we added 2,2,6,6-tetramethyl-1-piperidinyloxyl (TEMPO) to the standard reaction, it completely impeded the generation of 3aa, and the TEMPO adduct 6 was detected by HRMS analysis, indicating that a benzyl radical might be involved in this reaction (Scheme [4]A). We then used deuterium oxide (D2O) to determine other key intermediates of this transformation. With 20 equivalents of D2O, the D-labeled product 7 was obtained in 74% yield with 84% deuterium incorporation, suggesting that the benzyl carbanion might be a key intermediate in undergoing nucleophilic attack (Scheme [4]B).
Based on previous reports in the literature[3] [10d] and our mechanistic experiments, a possible mechanism is proposed, taking the reductive coupling reaction of 1a with 2a as an example (Scheme [5]). The photocatalyst 3DPAFIPN is excited by blue LEDs and then reductively quenched by DIPEA to generate 3DPAFIPN•– and DIPEA•+. 3DPAFIPN•– might be further excited through consecutive photoinduced electron transfer[10d] to form 3DPAFIPN•–*, a strong reductant, for SET reduction of 1a. After the reduction, the radical-anion intermediate I smoothly undergoes C–N bond cleavage to deliver the benzyl radical intermediate II. Another photocatalytic single-electron transfer process, which might precede or be coupled with the protonation, occurs to reduce intermediate II to the benzyl anion intermediate III. Finally, nucleophilic attack on the aldehyde 2a and subsequent protonation during workup provide the designed product 3aa.
In conclusion, we have established a photocatalytic Barbier-type reaction of aziridines and azetidines with nonactivated aldehydes, providing an efficient method for the synthesis of various pharmacologically useful amino alcohol derivatives.[16] The scope of the reaction encompasses a wide range of 2-arylaziridines, 2-arylazetidines, and nonactivated aldehydes. Moreover, this visible-light photocatalytic method features mild and transition-metal-free reaction conditions. Mechanistic studies indicated that benzyl radicals and benzyl anions are key intermediates.
#
Conflict of Interest
The authors declare no conflict of interest.
Supporting Information
- Supporting information for this article is available online at https://doi-org.accesdistant.sorbonne-universite.fr/10.1055/a-2039-9942.
- Supporting Information
-
References and Notes
- 1a Metal Catalyzed Reductive C–C Bond Formation: A Departure from Preformed Organometallic Reagents. Krische M. J; Springer: Berlin: 2007
- 1b Brahmachari G. RSC Adv. 2016; 6: 64676
- 1c Yi L, Ji T, Chen K.-Q, Chen X.-Y, Rueping M. CCS Chem. 2022; 4: 9
- 2a Barbier P. C. R. Hebd. Seances Acad. Sci. 1899; 128: 110
- 2b Nokami J, Otera J, Sudo T, Okawara R. Organometallics 1983; 2: 191
- 2c Yamamoto Y, Asao N. Chem. Rev. 1993; 93: 2207
- 2d Li C.-J. Tetrahedron 1996; 52: 5643
- 2e Li C.-J, Zhang W.-C. J. Am. Chem. Soc. 1998; 120: 9102
- 2f Keinicke L, Fristrup P, Norrby P.-O, Madsen R. J. Am. Chem. Soc. 2005; 127: 15756
- 2g Frimpong K, Wzorek J, Lawlor C, Spencer K, Mitzel T. J. Org. Chem. 2009; 74: 5861
- 3a Ravelli D, Protti S, Fagnoni M. Chem. Rev. 2016; 116: 9850
- 3b Pitzer L, Schwarz JL, Glorius F. Chem. Sci. 2019; 10: 8285
- 3c Wiles RJ, Molander GA. Isr. J. Chem. 2020; 60: 281
- 3d Donabauer K, König B. Acc. Chem. Res. 2021; 54: 242
- 3e Ye J.-H, Ju T, Huang H, Liao L.-L, Yu D.-G. Acc. Chem. Res. 2021; 54: 2518
- 3f Ran C.-K, Xiao H.-Z, Liao L.-L, Ju T, Zhang W, Yu D.-G. Natl. Sci. Open 2022; 2: 20220024 ; DOI: 10.1360/nso/20220024
- 3g Dou D, Wang T.-M, Li S.-F, Fang L.-J, Zhai H.-B, Cheng B. Youji Huaxue 2022; 42: 4257 ; For selected examples, see
- 3h Yatham VR, Shen Y, Martin R. Angew. Chem. Int. Ed. 2017; 56: 10915
- 3i Phelan JP, Lang SB, Compton JS, Kelly CB, Dykstra R, Gutierrez O, Molander GA. J. Am. Chem. Soc. 2018; 140: 8037
- 3j Ju T, Fu Q, Ye J.-H, Zhang Z, Liao L.-L, Yan S.-S, Tian X.-Y, Luo S.-P, Li J, Yu D.-G. Angew. Chem. Int. Ed. 2018; 57: 13897
- 3k Fu Q, Bo Z.-Y, Ye J.-H, Ju T, Huang H, Liao L.-L, Yu D.-G. Nat. Commun. 2019; 10: 3592
- 3l Meng Q.-YSchirmer T. E, Berger AL, Donabauer K, König B. J. Am. Chem. Soc. 2019; 141: 11393
- 3m Zhou W.-J, Wang Z.-H, Liao L.-L, Jiang Y.-X, Cao K.-G, Ju T, Li Y, Cao G.-M, Yu D.-G. Nat. Commun. 2020; 11: 3263
- 3n Song L, Fu D.-M, Chen L, Jiang Y.-X, Ye J.-H, Zhu L, Lan Y, Fu Q, Yu D.-G. Angew. Chem. Int. Ed. 2020; 59: 21121
- 3o Jiang Y.-X, Chen L, Ran C.-K, Song L, Zhang W, Liao L.-L, Yu D.-G. ChemSusChem 2020; 13: 6312
- 3p Liao L.-L, Cao G.-M, Jiang Y.-X, Jin X.-H, Hu X.-L, Chruma JJ, Sun G.-Q, Gui Y.-Y, Yu D.-G. J. Am. Chem. Soc. 2021; 143: 2812
- 3q Niu Y.-N, Jin X.-H, Liao L.-L, Huang H, Yu B, Yu Y.-M, Yu D.-G. Sci. China Chem. 2021; 64: 1164
- 3r Cao G.-M, Hu X.-L, Liao L.-L, Yan S.-S, Song L, Chruma JJ, Gong L, Yu D.-G. Nat. Commun. 2021; 12: 3306
- 3s Ju T, Zhou Y.-Q, Cao K.-G, Fu Q, Ye J.-H, Sun G.-Q, Liu X.-F, Chen L, Liao L.-L, Yu D.-G. Nat. Catal. 2021; 4: 304
- 3t Yan S.-S, Liu S.-H, Chen L, Bo Z.-Y, Jing K, Gao T.-Y, Yu B, Lan Y, Luo S.-P, Yu D.-G. Chem 2021; 7: 3099
- 3u Murugesan K, Donabauer K, Narobe R, Derdau V, Bauer A, König B. ACS Catal. 2022; 12: 3974
- 3v Jing K, Wei M.-K, Yan S.-S, Liao L.-L, Niu Y.-N, Luo S.-P, Yu B, Yu D.-G. Chin. J. Catal. 2022; 43: 1667
- 3w Ran C.-K, Niu Y.-N, Song L, Wei M.-K, Cao Y.-F, Luo S.-P, Yu Y.-M, Liao L.-L, Yu D.-G. ACS Catal. 2022; 12: 18
- 3x Bo Z.-Y, Yan S.-S, Gao T.-Y, Song L, Ran C.-K, He Y, Zhang W, Cao G.-M, Yu D.-G. Chin. J. Catal. 2022; 43: 2388
- 4a Liao L.-L, Cao G.-M, Ye J.-H, Sun G.-Q, Zhou W.-J, Gui Y.-Y, Yan S.-S, Shen G, Yu D.-G. J. Am. Chem. Soc. 2018; 140: 17338
- 4b Berger AL, Donabauer K, König B. Chem. Sci. 2018; 9: 7230
- 4c Berger AL, Donabauer K, König B. Chem. Sci. 2019; 10: 10991
- 4d Wang S, Cheng B.-Y, Sršen M, König B. J. Am. Chem. Soc. 2020; 142: 7524
- 4e Zhang L, Chu Y, Ma P, Zhao S, Li Q, Chen B, Hong X, Sun J. Org. Biomol. Chem. 2020; 18: 1073
- 5a Couty F, Evano G. Synlett 2009; 3053
- 5b Taylor RD, MacCoss M, Lawson AD. G. J. Med. Chem. 2014; 57: 5845
- 5c Singh GS. Mini-Rev. Med. Chem. 2016; 16: 892
- 5d Mehra V, Lumb I, Anand A, Kumar V. RSC Adv. 2017; 7: 45763
- 5e Blakemore DC, Castro L, Churcher I, Rees DC, Thomas AW, Wilson DM, Wood A. Nat. Chem. 2018; 10: 383
- 5f Fu Z, Xu J. Huaxue Jinzhan 2018; 30: 1047
- 6a Singh GS. Adv. Heterocycl. Chem. 2019; 129: 245
- 6b Singh GS. Adv. Heterocycl. Chem. 2020; 130: 1
- 6c Mughal H, Szostak M. Org. Biomol. Chem. 2021; 19: 3274
- 7a Stanković S, D’hooghe M, Catak S, Eum H, Waroquier M, Van Speybroeck V, De Kimpe N, Ha H.-J. Chem. Soc. Rev. 2012; 41: 643
- 7b Chen X, Xu J. Huaxue Jinzhan 2017; 29: 181
- 7c Chu X, Chang H, Gao W, Wei W, Li X. Youji Huaxue 2017; 37: 2569
- 7d Smolobochkin AV, Gazizov AS, Burilov AR, Pudovik MA, Sinyashin OG. Russ. Chem. Rev. 2019; 88: 1104
- 7e Huo M, Bian Y, Yu C. Sci. China Chem. 2021; 64: 1778
- 7f Du Q, Zhang L, Gao F, Wang L, Zhang W. Youji Huaxue 2022; 42: 3240
- 8 Wang C. Synthesis 2017; 49: 5307
- 9a Almena J, Foubelo F, Yus M. Tetrahedron 1994; 50: 5775
- 9b Almena J, Foubelo F, Yus M. J. Org. Chem. 1994; 59: 3210
- 9c Ohno H, Hamaguchi H, Tanaka T. Org. Lett. 2000; 2: 2161
- 9d Takemoto Y, Anzai M, Yanada R, Fujii N, Ohno H, Ibuka T. Tetrahedron Lett. 2001; 42: 1725
- 9e Shimizu M, Nishiura S, Hachiya I. Heterocycles 2007; 74: 177
- 9f Woods BP, Orlandi M, Huang C.-Y, Sigman MS, Doyle AG. J. Am. Chem. Soc. 2017; 139: 5688
- 9g Zhang Y.-Q, Vogelsang E, Qu Z.-W, Grimme S, Gansäuer A. Angew. Chem. Int. Ed. 2017; 56: 12654
- 9h Davies J, Janssen-Müller D, Zimin DP, Day CS, Yanagi T, Elfert J, Martin R. J. Am. Chem. Soc. 2021; 143: 4949
- 10a Larraufie M.-H, Pellet R, Fensterbank L, Goddard J.-P, Lacôte E, Malacria M, Ollivier C. Angew. Chem. Int. Ed. 2011; 50: 4463
- 10b Steiman TJ, Liu J, Mengiste A, Doyle AG. J. Am. Chem. Soc. 2020; 142: 7598
- 10c Xu C.-H, Li J.-H, Xiang J.-N, Deng W. Org. Lett. 2021; 23: 3696
- 10d Chen L, Qu Q, Ran C.-K, Wang W, Zhang W, He Y, Liao L.-L, Ye J.-H, Yu D.-G. Angew. Chem. Int. Ed. 2023; 62: e202217918
- 11a Foley VM, McSweeney CM, Eccles KS, Lawrence SE, McGlacken GP. Org. Lett. 2015; 17: 5642
- 11b Tejo C, See YF. A, Mathiew M, Chan PW. H. Org. Biomol. Chem. 2016; 14: 844
- 11c Zhang Y.-Q, Bohle F, Bleith R, Schnakenburg G, Grimme S, Gansäuer A. Angew. Chem. Int. Ed. 2018; 57: 13528
- 11d Wang X.-M, Liu Y.-W, Ma R.-J, Si C.-M, Wei B.-G. J. Org. Chem. 2019; 84: 11261
- 11e Ichikawa S, Buchwald SL. Org. Lett. 2019; 21: 8736
- 12a Ishitani O, Pac C, Sakurai H. J. Org. Chem. 1983; 48: 2941
- 12b Nakajima M, Fava E, Loescher S, Jiang Z, Rueping M. Angew. Chem. Int. Ed. 2015; 54: 8828
- 12c Annibaletto J, Jacob C, Theunissen C. Org. Lett. 2022; 24: 4170
- 13a Ouyang K, Hao W, Zhang W.-X, Xi Z. Chem. Rev. 2015; 115: 12045
- 13b Wang Q, Su Y, Li L, Huang H. Chem. Soc. Rev. 2016; 45: 1257
- 13c Wang Y, Li F, Zeng Q. Acta Chim. Sin. (Engl. Ed.) 2022; 80: 386
- 14a Bamou FZ, Le TM, Volford B, Szekeres A, Szakonyi Z. Molecules 2020; 25: 21
- 14b Yang D, Xie C.-X, Wu X.-T, Fei L.-R, Feng L, Ma C. J. Org. Chem. 2020; 85: 14905
- 14c You H.-Y, Vegi SR, Lagishetti C, Chen S, Reddy RS, Yang XH, Guo J, Wang CH, He Y. J. Org. Chem. 2018; 83: 4119
- 14d Ma R, Young J, Promontorio R, Dannheim FM, Pattillo CC, White MC. J. Am. Chem. Soc. 2019; 141: 9468
- 14e Reddy RS, Zheng S, Lagishetti C, Youa H, He Y. RSC Adv. 2016; 6: 68199
- 14f Heravi MM, Lashaki TB, Fattahi B, Zadsirjan V. RSC Adv. 2018; 8: 6634
- 14g Pomplun S, Shugrue CR, Schmitt AM, Schissel CK, Farquhar CE, Pentelute BL. Angew. Chem. Int. Ed. 2020; 59: 11566
- 14h Reddy RS, Lagishetti C, Kiran IN. C, You H, He Y. Org. Lett. 2016; 18: 3818
- 14i Cossy J, Pardo DG, Dumas C, Mirguet O, Déchamps I, Métro T.-X, Burger B, Roudeau R, Appenzeller J, Cochi A. Chirality 2009; 21: 850
- 14j Chowdari NS, Ramachary DB, Barbas CF. Org. Lett. 2003; 5: 1685
- 14k Raji M, Le TM, Csámpai A, Nagy V, Zupkó I, Szakonyi Z. Synthesis 2022; 54: 3831
- 14l Mao P, Yang L, Xiao Y, Yuan J, Mai W, Gao J, Zhang X. Youji Huaxue 2019; 39: 443
- 14m Inuki S, Sato K, Fujimoto Y. Tetrahedron Lett. 2015; 56: 5787
- 14n Lagishetti C, Banne S, You H, Tang M, Guo J, Qi N, He Y. Org. Lett. 2019; 21: 5301
- 14o Shinichi I, Yoshiki S, Koichi I, Akira H, Seiichi N. Bull. Chem. Soc. Jpn. 1987; 60: 395
- 14p Zhou Z, Tan Y, Shen X. Sci. China Chem. 2021; 64: 452
- 15 Sterling AJ, Smith RC, Anderson EA, Duarte F. Chem. Rxiv. 2022; preprint; DOI:
- 16 tert-Butyl (3-Biphenyl-4-yl-4-hydroxy-6-phenylhexyl)carbamate ( 3aa): Typical ProcedureAn oven-dried Schlenk tube (10 mL) containing a stirring bar was charged with the 1a (0.2 mmol, 61.9 mg, 1 equiv) and 3DPAFIPN (0.004 mmol, 2.6 mg, 2 mol%). The Schlenk tube was then transferred to a glovebox where it was charged with PivOK (0.2 mmol, 28 mg, 1 equiv). The tube was taken out of the glovebox, connected to a vacuum line, and evacuated and back-filled with N2 three times. 2a (0.4 mmol, 53.7 mg, 2 equiv), DIPEA (0.4 mmol, 51.7 mg, 2 equiv), and DMA (2 mL) were then added under flowing N2. Finally, the mixture in the sealed tube was placed 1 cm from a 30 W blue LED lamp and stirred at rt (25 °C) for 36 h. The reaction was quenched with 2 N aq HCl (2 mL), and the mixture was extracted with EtOAc. The extracts were concentrated in vacuo and the residue was purified by flash chromatography [silica gel, PE–EtOAc (10:1 to 3:1)] to give a light yellow viscous liquid; yield: 73 mg (82%). 1H NMR (400 MHz, CDCl3, mixture of two diastereomers): δ = 7.61–7.48 (m, 4 H), 7.46–7.38 (m, 2 H), 7.35–7.12 (m, 7 H), 7.11–7.06 (m, 1 H), 4.57–4.44 (m, 1 H), 3.84–3.69 (m, 1 H), 3.15–2.88 (m, 2 H), 2.87–2.76 (m, 1 H), 2.73–2.55 (m, 2 H), 2.21–2.09 (m, 1 H), 1.98–1.80 (m, 2 H), 1.76–1.53 (m, 2 H), 1.41 (s, 9 H). 13C NMR (101 MHz, CDCl3, mixture of two diastereomers): δ = 156.2, 156.1, 142.14, 142.06, 140.93, 140.88, 140.86, 140.0, 139.7, 139.5, 129.4, 128.9, 128.8, 128.6, 128.54, 128.52, 128.47, 127.48, 127.47, 127.34, 127.31, 127.11, 127.09, 126.0, 125.9, 79.3, 75.1, 74.2, 49.9, 49.3, 39.2, 37.1, 36.8, 32.6, 32.4, 32.3, 32.0, 28.5. HRMS (ESI+): m/z [M + Na]+ calcd for C29H35NNaO3: 468.2509; found: 468.2506.
For selected reviews, see:
Corresponding Authors
Publication History
Received: 25 January 2023
Accepted after revision: 21 February 2023
Accepted Manuscript online:
21 February 2023
Article published online:
08 March 2023
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References and Notes
- 1a Metal Catalyzed Reductive C–C Bond Formation: A Departure from Preformed Organometallic Reagents. Krische M. J; Springer: Berlin: 2007
- 1b Brahmachari G. RSC Adv. 2016; 6: 64676
- 1c Yi L, Ji T, Chen K.-Q, Chen X.-Y, Rueping M. CCS Chem. 2022; 4: 9
- 2a Barbier P. C. R. Hebd. Seances Acad. Sci. 1899; 128: 110
- 2b Nokami J, Otera J, Sudo T, Okawara R. Organometallics 1983; 2: 191
- 2c Yamamoto Y, Asao N. Chem. Rev. 1993; 93: 2207
- 2d Li C.-J. Tetrahedron 1996; 52: 5643
- 2e Li C.-J, Zhang W.-C. J. Am. Chem. Soc. 1998; 120: 9102
- 2f Keinicke L, Fristrup P, Norrby P.-O, Madsen R. J. Am. Chem. Soc. 2005; 127: 15756
- 2g Frimpong K, Wzorek J, Lawlor C, Spencer K, Mitzel T. J. Org. Chem. 2009; 74: 5861
- 3a Ravelli D, Protti S, Fagnoni M. Chem. Rev. 2016; 116: 9850
- 3b Pitzer L, Schwarz JL, Glorius F. Chem. Sci. 2019; 10: 8285
- 3c Wiles RJ, Molander GA. Isr. J. Chem. 2020; 60: 281
- 3d Donabauer K, König B. Acc. Chem. Res. 2021; 54: 242
- 3e Ye J.-H, Ju T, Huang H, Liao L.-L, Yu D.-G. Acc. Chem. Res. 2021; 54: 2518
- 3f Ran C.-K, Xiao H.-Z, Liao L.-L, Ju T, Zhang W, Yu D.-G. Natl. Sci. Open 2022; 2: 20220024 ; DOI: 10.1360/nso/20220024
- 3g Dou D, Wang T.-M, Li S.-F, Fang L.-J, Zhai H.-B, Cheng B. Youji Huaxue 2022; 42: 4257 ; For selected examples, see
- 3h Yatham VR, Shen Y, Martin R. Angew. Chem. Int. Ed. 2017; 56: 10915
- 3i Phelan JP, Lang SB, Compton JS, Kelly CB, Dykstra R, Gutierrez O, Molander GA. J. Am. Chem. Soc. 2018; 140: 8037
- 3j Ju T, Fu Q, Ye J.-H, Zhang Z, Liao L.-L, Yan S.-S, Tian X.-Y, Luo S.-P, Li J, Yu D.-G. Angew. Chem. Int. Ed. 2018; 57: 13897
- 3k Fu Q, Bo Z.-Y, Ye J.-H, Ju T, Huang H, Liao L.-L, Yu D.-G. Nat. Commun. 2019; 10: 3592
- 3l Meng Q.-YSchirmer T. E, Berger AL, Donabauer K, König B. J. Am. Chem. Soc. 2019; 141: 11393
- 3m Zhou W.-J, Wang Z.-H, Liao L.-L, Jiang Y.-X, Cao K.-G, Ju T, Li Y, Cao G.-M, Yu D.-G. Nat. Commun. 2020; 11: 3263
- 3n Song L, Fu D.-M, Chen L, Jiang Y.-X, Ye J.-H, Zhu L, Lan Y, Fu Q, Yu D.-G. Angew. Chem. Int. Ed. 2020; 59: 21121
- 3o Jiang Y.-X, Chen L, Ran C.-K, Song L, Zhang W, Liao L.-L, Yu D.-G. ChemSusChem 2020; 13: 6312
- 3p Liao L.-L, Cao G.-M, Jiang Y.-X, Jin X.-H, Hu X.-L, Chruma JJ, Sun G.-Q, Gui Y.-Y, Yu D.-G. J. Am. Chem. Soc. 2021; 143: 2812
- 3q Niu Y.-N, Jin X.-H, Liao L.-L, Huang H, Yu B, Yu Y.-M, Yu D.-G. Sci. China Chem. 2021; 64: 1164
- 3r Cao G.-M, Hu X.-L, Liao L.-L, Yan S.-S, Song L, Chruma JJ, Gong L, Yu D.-G. Nat. Commun. 2021; 12: 3306
- 3s Ju T, Zhou Y.-Q, Cao K.-G, Fu Q, Ye J.-H, Sun G.-Q, Liu X.-F, Chen L, Liao L.-L, Yu D.-G. Nat. Catal. 2021; 4: 304
- 3t Yan S.-S, Liu S.-H, Chen L, Bo Z.-Y, Jing K, Gao T.-Y, Yu B, Lan Y, Luo S.-P, Yu D.-G. Chem 2021; 7: 3099
- 3u Murugesan K, Donabauer K, Narobe R, Derdau V, Bauer A, König B. ACS Catal. 2022; 12: 3974
- 3v Jing K, Wei M.-K, Yan S.-S, Liao L.-L, Niu Y.-N, Luo S.-P, Yu B, Yu D.-G. Chin. J. Catal. 2022; 43: 1667
- 3w Ran C.-K, Niu Y.-N, Song L, Wei M.-K, Cao Y.-F, Luo S.-P, Yu Y.-M, Liao L.-L, Yu D.-G. ACS Catal. 2022; 12: 18
- 3x Bo Z.-Y, Yan S.-S, Gao T.-Y, Song L, Ran C.-K, He Y, Zhang W, Cao G.-M, Yu D.-G. Chin. J. Catal. 2022; 43: 2388
- 4a Liao L.-L, Cao G.-M, Ye J.-H, Sun G.-Q, Zhou W.-J, Gui Y.-Y, Yan S.-S, Shen G, Yu D.-G. J. Am. Chem. Soc. 2018; 140: 17338
- 4b Berger AL, Donabauer K, König B. Chem. Sci. 2018; 9: 7230
- 4c Berger AL, Donabauer K, König B. Chem. Sci. 2019; 10: 10991
- 4d Wang S, Cheng B.-Y, Sršen M, König B. J. Am. Chem. Soc. 2020; 142: 7524
- 4e Zhang L, Chu Y, Ma P, Zhao S, Li Q, Chen B, Hong X, Sun J. Org. Biomol. Chem. 2020; 18: 1073
- 5a Couty F, Evano G. Synlett 2009; 3053
- 5b Taylor RD, MacCoss M, Lawson AD. G. J. Med. Chem. 2014; 57: 5845
- 5c Singh GS. Mini-Rev. Med. Chem. 2016; 16: 892
- 5d Mehra V, Lumb I, Anand A, Kumar V. RSC Adv. 2017; 7: 45763
- 5e Blakemore DC, Castro L, Churcher I, Rees DC, Thomas AW, Wilson DM, Wood A. Nat. Chem. 2018; 10: 383
- 5f Fu Z, Xu J. Huaxue Jinzhan 2018; 30: 1047
- 6a Singh GS. Adv. Heterocycl. Chem. 2019; 129: 245
- 6b Singh GS. Adv. Heterocycl. Chem. 2020; 130: 1
- 6c Mughal H, Szostak M. Org. Biomol. Chem. 2021; 19: 3274
- 7a Stanković S, D’hooghe M, Catak S, Eum H, Waroquier M, Van Speybroeck V, De Kimpe N, Ha H.-J. Chem. Soc. Rev. 2012; 41: 643
- 7b Chen X, Xu J. Huaxue Jinzhan 2017; 29: 181
- 7c Chu X, Chang H, Gao W, Wei W, Li X. Youji Huaxue 2017; 37: 2569
- 7d Smolobochkin AV, Gazizov AS, Burilov AR, Pudovik MA, Sinyashin OG. Russ. Chem. Rev. 2019; 88: 1104
- 7e Huo M, Bian Y, Yu C. Sci. China Chem. 2021; 64: 1778
- 7f Du Q, Zhang L, Gao F, Wang L, Zhang W. Youji Huaxue 2022; 42: 3240
- 8 Wang C. Synthesis 2017; 49: 5307
- 9a Almena J, Foubelo F, Yus M. Tetrahedron 1994; 50: 5775
- 9b Almena J, Foubelo F, Yus M. J. Org. Chem. 1994; 59: 3210
- 9c Ohno H, Hamaguchi H, Tanaka T. Org. Lett. 2000; 2: 2161
- 9d Takemoto Y, Anzai M, Yanada R, Fujii N, Ohno H, Ibuka T. Tetrahedron Lett. 2001; 42: 1725
- 9e Shimizu M, Nishiura S, Hachiya I. Heterocycles 2007; 74: 177
- 9f Woods BP, Orlandi M, Huang C.-Y, Sigman MS, Doyle AG. J. Am. Chem. Soc. 2017; 139: 5688
- 9g Zhang Y.-Q, Vogelsang E, Qu Z.-W, Grimme S, Gansäuer A. Angew. Chem. Int. Ed. 2017; 56: 12654
- 9h Davies J, Janssen-Müller D, Zimin DP, Day CS, Yanagi T, Elfert J, Martin R. J. Am. Chem. Soc. 2021; 143: 4949
- 10a Larraufie M.-H, Pellet R, Fensterbank L, Goddard J.-P, Lacôte E, Malacria M, Ollivier C. Angew. Chem. Int. Ed. 2011; 50: 4463
- 10b Steiman TJ, Liu J, Mengiste A, Doyle AG. J. Am. Chem. Soc. 2020; 142: 7598
- 10c Xu C.-H, Li J.-H, Xiang J.-N, Deng W. Org. Lett. 2021; 23: 3696
- 10d Chen L, Qu Q, Ran C.-K, Wang W, Zhang W, He Y, Liao L.-L, Ye J.-H, Yu D.-G. Angew. Chem. Int. Ed. 2023; 62: e202217918
- 11a Foley VM, McSweeney CM, Eccles KS, Lawrence SE, McGlacken GP. Org. Lett. 2015; 17: 5642
- 11b Tejo C, See YF. A, Mathiew M, Chan PW. H. Org. Biomol. Chem. 2016; 14: 844
- 11c Zhang Y.-Q, Bohle F, Bleith R, Schnakenburg G, Grimme S, Gansäuer A. Angew. Chem. Int. Ed. 2018; 57: 13528
- 11d Wang X.-M, Liu Y.-W, Ma R.-J, Si C.-M, Wei B.-G. J. Org. Chem. 2019; 84: 11261
- 11e Ichikawa S, Buchwald SL. Org. Lett. 2019; 21: 8736
- 12a Ishitani O, Pac C, Sakurai H. J. Org. Chem. 1983; 48: 2941
- 12b Nakajima M, Fava E, Loescher S, Jiang Z, Rueping M. Angew. Chem. Int. Ed. 2015; 54: 8828
- 12c Annibaletto J, Jacob C, Theunissen C. Org. Lett. 2022; 24: 4170
- 13a Ouyang K, Hao W, Zhang W.-X, Xi Z. Chem. Rev. 2015; 115: 12045
- 13b Wang Q, Su Y, Li L, Huang H. Chem. Soc. Rev. 2016; 45: 1257
- 13c Wang Y, Li F, Zeng Q. Acta Chim. Sin. (Engl. Ed.) 2022; 80: 386
- 14a Bamou FZ, Le TM, Volford B, Szekeres A, Szakonyi Z. Molecules 2020; 25: 21
- 14b Yang D, Xie C.-X, Wu X.-T, Fei L.-R, Feng L, Ma C. J. Org. Chem. 2020; 85: 14905
- 14c You H.-Y, Vegi SR, Lagishetti C, Chen S, Reddy RS, Yang XH, Guo J, Wang CH, He Y. J. Org. Chem. 2018; 83: 4119
- 14d Ma R, Young J, Promontorio R, Dannheim FM, Pattillo CC, White MC. J. Am. Chem. Soc. 2019; 141: 9468
- 14e Reddy RS, Zheng S, Lagishetti C, Youa H, He Y. RSC Adv. 2016; 6: 68199
- 14f Heravi MM, Lashaki TB, Fattahi B, Zadsirjan V. RSC Adv. 2018; 8: 6634
- 14g Pomplun S, Shugrue CR, Schmitt AM, Schissel CK, Farquhar CE, Pentelute BL. Angew. Chem. Int. Ed. 2020; 59: 11566
- 14h Reddy RS, Lagishetti C, Kiran IN. C, You H, He Y. Org. Lett. 2016; 18: 3818
- 14i Cossy J, Pardo DG, Dumas C, Mirguet O, Déchamps I, Métro T.-X, Burger B, Roudeau R, Appenzeller J, Cochi A. Chirality 2009; 21: 850
- 14j Chowdari NS, Ramachary DB, Barbas CF. Org. Lett. 2003; 5: 1685
- 14k Raji M, Le TM, Csámpai A, Nagy V, Zupkó I, Szakonyi Z. Synthesis 2022; 54: 3831
- 14l Mao P, Yang L, Xiao Y, Yuan J, Mai W, Gao J, Zhang X. Youji Huaxue 2019; 39: 443
- 14m Inuki S, Sato K, Fujimoto Y. Tetrahedron Lett. 2015; 56: 5787
- 14n Lagishetti C, Banne S, You H, Tang M, Guo J, Qi N, He Y. Org. Lett. 2019; 21: 5301
- 14o Shinichi I, Yoshiki S, Koichi I, Akira H, Seiichi N. Bull. Chem. Soc. Jpn. 1987; 60: 395
- 14p Zhou Z, Tan Y, Shen X. Sci. China Chem. 2021; 64: 452
- 15 Sterling AJ, Smith RC, Anderson EA, Duarte F. Chem. Rxiv. 2022; preprint; DOI:
- 16 tert-Butyl (3-Biphenyl-4-yl-4-hydroxy-6-phenylhexyl)carbamate ( 3aa): Typical ProcedureAn oven-dried Schlenk tube (10 mL) containing a stirring bar was charged with the 1a (0.2 mmol, 61.9 mg, 1 equiv) and 3DPAFIPN (0.004 mmol, 2.6 mg, 2 mol%). The Schlenk tube was then transferred to a glovebox where it was charged with PivOK (0.2 mmol, 28 mg, 1 equiv). The tube was taken out of the glovebox, connected to a vacuum line, and evacuated and back-filled with N2 three times. 2a (0.4 mmol, 53.7 mg, 2 equiv), DIPEA (0.4 mmol, 51.7 mg, 2 equiv), and DMA (2 mL) were then added under flowing N2. Finally, the mixture in the sealed tube was placed 1 cm from a 30 W blue LED lamp and stirred at rt (25 °C) for 36 h. The reaction was quenched with 2 N aq HCl (2 mL), and the mixture was extracted with EtOAc. The extracts were concentrated in vacuo and the residue was purified by flash chromatography [silica gel, PE–EtOAc (10:1 to 3:1)] to give a light yellow viscous liquid; yield: 73 mg (82%). 1H NMR (400 MHz, CDCl3, mixture of two diastereomers): δ = 7.61–7.48 (m, 4 H), 7.46–7.38 (m, 2 H), 7.35–7.12 (m, 7 H), 7.11–7.06 (m, 1 H), 4.57–4.44 (m, 1 H), 3.84–3.69 (m, 1 H), 3.15–2.88 (m, 2 H), 2.87–2.76 (m, 1 H), 2.73–2.55 (m, 2 H), 2.21–2.09 (m, 1 H), 1.98–1.80 (m, 2 H), 1.76–1.53 (m, 2 H), 1.41 (s, 9 H). 13C NMR (101 MHz, CDCl3, mixture of two diastereomers): δ = 156.2, 156.1, 142.14, 142.06, 140.93, 140.88, 140.86, 140.0, 139.7, 139.5, 129.4, 128.9, 128.8, 128.6, 128.54, 128.52, 128.47, 127.48, 127.47, 127.34, 127.31, 127.11, 127.09, 126.0, 125.9, 79.3, 75.1, 74.2, 49.9, 49.3, 39.2, 37.1, 36.8, 32.6, 32.4, 32.3, 32.0, 28.5. HRMS (ESI+): m/z [M + Na]+ calcd for C29H35NNaO3: 468.2509; found: 468.2506.
For selected reviews, see:
