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DOI: 10.1055/a-2155-3498
Recent Developments on the Synthesis of Sulfoxides via Sulfenate Anions
This work was supported by the Walter Benjamin Program (500656103) of the Deutsche Forschungsgemeinschaft.
Abstract
Since the early 2000s, novel synthetic methods for the preparation of sulfoxides have emerged that involve sulfenate anions as sulfur nucleophiles. This short review showcases key advances in these sulfenate protocols, including catalytic enantioselective alkylation and arylation, and provides future directions for this research field.
1 Introduction
2 Precursors of Sulfenate Anions
3 Organocatalytic Enantioselective Alkylation of Sulfenate Anions
4 Palladium-Catalyzed Arylation of Sulfenate Anions
5 Coupling of Sulfenate Anions with Hypervalent Iodine Reagents
6 Conclusions and Outlook
# 1
Introduction
Sulfoxides are of high value for various applications, such as drugs,[1] ligands in transition-metal catalysis,[2] and chiral auxiliaries.[3] The versatility of this class of sulfur motifs has inspired tremendous efforts toward their synthesis. Traditionally, sulfoxides have been synthesized via two well-established approaches: (1) oxidation of sulfides, and (2) nucleophilic substitution of sulfinyl compounds, such as sulfinate esters, with organometallic reagents. These protocols allow not only the routine preparation of racemic sulfoxides but also the production of enantioenriched (or enantiopure) sulfoxides. However, these canonical methods have some key shortcomings. For example, the catalytic enantioselective oxidation of sulfides requires substrates bearing two sterically distinct substituents to achieve high enantioselectivity,[4] and the use of strong oxidants can cause overoxidation to give sulfones.[5] Nucleophilic substitution of sulfinyl compounds (a process known as the Andersen method) requires the diastereoselective preparation of sulfinyl substrates along with their tedious purification.[6]
The creation of a C–S bond between sulfenate anions and carbon electrophiles has emerged as a novel methodology for synthesizing sulfoxides over the past two decades. Alkylation with reactive electrophiles, such as benzyl bromides and methyl iodide, is the simplest and most facile method to convert sulfenate anions into sulfoxides. In fact, sulfenate alkylation has often been used as an indirect method to prove the intermediacy of sulfenate anions in a given transformation.[7] Beyond simple alkylation, sulfenate anions have become amenable to a range of transformations for the construction of sulfoxides. In this article, recent developments in sulfoxide synthesis via sulfenate anion chemistry are reviewed, focusing on three types of transformation: (1) organocatalytic enantioselective alkylation, (2) palladium-catalyzed arylation, and (3) transition-metal-free coupling. The current scope and limitations are presented, along with opportunities for future developments in this research field. For a more comprehensive review of sulfenate anion chemistry in synthesis, the reader is referred to a recent article by Schwan and co-workers.[8] Additionally, the reader is directed to other noteworthy review articles, wherein the synthesis of sulfoxides involving sulfenate anions is discussed.[9] [10] It is also important to note that the utilization of sulfenate anions as organocatalysts represents another burgeoning area of research that has been pioneered by the Walsh group.[11]
# 2
Precursors of Sulfenate Anions
Sulfenate anions (RSO–) are unstable reactive species that are generated in situ for synthetic use. It is important to note that sulfenic acids (RSOH) are also unstable species; deprotonation of sulfenic acids, seemingly the most straightforward method to generate sulfenate anions, is feasible only in limited cases where sulfenic acids are produced in situ.[12] Over the last 20 years, various sulfoxides have been developed as viable sources of sulfenate anions. These readily prepared sulfenate precursors have paved the way for convenient methods to access sulfenate anions, leading to a significant expansion of their synthetic applications, especially in the field of sulfoxide synthesis.
Perrio and co-workers were the first to develop alkoxycarbonylethyl sulfoxides of type A as precursors of sulfenate anions (Figure [1]).[13] Sulfoxides of type A can be readily synthesized in two steps from the corresponding thiols. Under basic conditions, sulfoxides of type A can undergo retro-Michael reactions to produce sulfenate anions. Perrio’s team demonstrated the release of both aryl and alkyl sulfenates, which could then be alkylated in situ to form sulfoxides. Sulfoxides of type A have since been extensively employed as sulfenate precursors. Another highly valuable sulfenate precursor is trimethylsilylethyl sulfoxides of type B, also introduced by the Perrio group.[14] These sulfoxides can be readily converted into sulfenate anions (along with ethylene) upon treatment with fluoride. Several other useful sulfenate precursors have been developed, for example, β-sulfinyl acrylates (type C)[15] release sulfenate anions upon the addition of nucleophiles, such as thiolates, via an addition–elimination mechanism. Sulfinyl sulfones (type D)[16] undergo retro-Michael reactions in the presence of a base (similar to sulfoxides of type A) to liberate sulfenate anions. Allyl sulfoxides (type E),[17] methyl sulfoxides (type F),[18] benzyl sulfoxides (type G),[19] and tert-butyl sulfoxides (type H)[20] have also been identified as viable sulfenate precursors; the use of these substrates in sulfoxide synthesis is discussed in the following sections. Finally, β-keto sulfoxides (type I)[21] are proposed to produce sulfenate anions through base-mediated α-benzylation, [2,3]-sigmatropic rearrangement, and deprotonation of the resultant sulfenic acids.
# 3
Organocatalytic Enantioselective Alkylation of Sulfenate Anions
Seminal work on organocatalytic enantioselective alkylation of sulfenate anions can be traced back to 2005. As mentioned in the previous section, Perrio and co-workers developed a general method to access sulfenate anions from ethoxycarbonylethyl sulfoxides of type A.[13] While investigating derivatization of the sulfenates with alkyl halides, Perrio’s research group studied the enantioselective alkylation of p-toluenesulfenate, derived from sulfoxide 1, in the presence of (–)-sparteine (Scheme [1]). Following sulfenate generation with n-BuLi, the chiral ligand was expected to coordinate with the lithium to create an asymmetric environment for C–S bond formation. This reaction gave rise to sulfoxide 2 in 54% yield and 23% ee. Despite the limited enantioselectivity and the stoichiometric use of the chiral ligand, this experiment demonstrated the potential for enantiocontrol through the countercation of sulfenate anions.
In 2011, the Perrio group advanced the concept of enantioselective alkylation of sulfenate anions through phase-transfer catalysis (Scheme [2]).[16] They identified arylsulfinyl sulfones of type D as the optimal sulfenate precursors. Among six commercial tetraalkylammonium salts tested, the cinchonidinium derivative 3 showed the highest enantioselectivity, forming aryl methyl sulfoxide 4 in 88% yield with 59% ee. The reaction was sensitive to alkyl electrophiles, as the use of benzyl bromide, for example, dropped the selectivity to 19% ee. In a subsequent paper by the same research group, this organocatalytic system was applied to the alkylation of alkanesulfenates, however, low to moderate enantioselectivity was observed (3 examples, 20–47% ee). [22]
A breakthrough in the field of organocatalytic alkylation of sulfenate anions was made by Tan, Kee, and co-workers (Scheme [3]).[23] They employed the novel chiral halogenated pentanidium salt 5 as a phase-transfer catalyst and showcased the synthesis of a remarkable collection of heteroaryl benzyl sulfoxides in high yields and enantioselectivities (34 examples, 73–99% yield, 71–99% ee). The reaction was successful with a range of alkyl electrophiles, such as allyl bromides and alkyl iodides, delivering sulfoxides with high enantioselectivities. Alkylation of an alkyl sulfenate was documented for only one case (tert-butylsulfenate), as a moderately enantioselective reaction (53% ee). This work stands as the current state-of-the-art method for achieving the highly enantioselective alkylation of heteroaryl sulfenate anions.
# 4
Palladium-Catalyzed Arylation of Sulfenate Anions
In 2006, the group of Poli and Madec reported the Pd-catalyzed allylic alkylation of sulfenate anions under biphasic conditions.[24] They advanced this chemistry to the first palladium-catalyzed arylation of sulfenate anions (Scheme [4]).[25] The reaction involved Pd2(dba)3, Xantphos as the ligand, and a toluene/water biphasic medium. The arylation of sulfenates, which were generated in situ from tert-butoxycarbonylethyl sulfoxides (type A), with aryl iodides resulted in the formation of sulfoxides in good yields (16 examples, 35–96% yield). When alkyl sulfenates were used as coupling substrates, the reaction typically gave sulfoxides in low to moderate yields. Note that this method was only applicable to aryl iodides (and one example of a vinyl iodide), and an attempt to couple with p-tolyl bromide was unsuccessful.
In the following year, Colobert, Abarca, and co-workers demonstrated an extension of the substrate scope.[26] They employed heteroaryl bromides as coupling partners under biphasic conditions, similar to the original Poli and Madec conditions, thus allowing for the synthesis of heteroaryl sulfoxides with pyridine, thiophene, and pyrimidine substituents.
One year after the publication of their racemic sulfoxide synthesis, Poli, Madec, and co-workers made a pioneering contribution to the enantioselective arylation of sulfenate anions (Scheme [5]).[27] By using the Josiphos-type ligand 6, arylation of sulfenate anions with aryl iodides gave enantioenriched sulfoxides in good yields (10 examples, 67–98% yield). However, the enantioselectivity of these reactions was typically low to moderate (0–80% ee); when o-iodoanisole was used, the formation of a racemic sulfoxide was observed.
The same research group also developed the arylation of sulfenate anions starting from allyl sulfoxides of type E as alternative sulfenate precursors (Scheme [6]).[17] Based on the Mislow–Braverman–Evans rearrangement ([2,3]-sigmatropic rearrangement between allyl sulfoxide and allylic sulfenate esters), a mechanistic scenario was formulated in which allylic sulfenate esters were captured with Pd(0) to form sulfenate anions and π-allylpalladium complexes. The latter were then trapped with KOt-Bu, identified as the optimal nucleophile for this purpose, to regenerate Pd(0) as the species responsible for the catalytic arylation of the sulfenate anions. Although the yields of the resulting sulfoxides were often moderate (13 examples, 15–60% yield), the coupling of simple aryl bromides was realized for the first time.
A new method to access sulfenate anions under palladium catalysis was discovered by Nolan and co-workers (Scheme [7]).[18] A Pd/NHC catalytic system, namely [Pd(IPr*)](cin)Cl], enabled the synthesis of aryl sulfoxides in moderate to good yields (17 examples, 34–85% yield) using aryl methyl sulfoxides of type F as precursors of sulfenate anions. A proposed mechanism involves two catalytic roles of the palladium complex. The first is the generation of sulfenate anions by sacrificing one equivalent of the aryl halide, while the second is the arylation of sulfenate anions with another equivalent of the aryl halide. In addition to aryl bromides, the reaction even allowed for the coupling of aryl chlorides. However, certain limitations were identified, as the desired sulfoxide products could not be obtained using ortho-substituted aryl bromides or electron-deficient aryl bromides, such as those bearing p-acetyl, p-nitro, and p-trifluoromethyl substituents.
In 2014, Walsh and co-workers elevated the synthetic utility of sulfenate arylation to the next level through a significant expansion of the substrate scope (Scheme [8]).[19] Using benzyl sulfoxides of type G as the sulfenate precursors, the Pd/NiXantPhos catalytic platform allowed for the use of a large variety of (hetero)aryl bromides, including 2-tolyl, 4-nitrophenyl, and pyridyl bromides (12 examples, 85–95% yield). Additionally, the scope of the sulfenate anions was also remarkable, and included those with 4-dimethylaminophenyl, 3-pyridyl, and 2-thienyl groups (11 examples, 85–99% yield). Of note, Walsh also demonstrated one example of an alkyl sulfenate, a cyclohexyl sulfenate anion, as a viable substrate for C–S bond-forming coupling.
A proposed mechanism initiates with the palladium-catalyzed formation of diarylmethyl sulfoxide 7 (Scheme [8]). This intermediate participates in the formation of palladium π-benzyl complex 8 and sulfenate anions. The former is trapped by NaOt-Bu to release Pd(0), which is involved in the arylation of sulfenate anions in another catalytic cycle. As is evident from the proposed mechanism, the use of benzyl sulfoxides of type G as sulfenate precursors necessitates the need for two equivalents of the aryl bromide to produce the target sulfoxides.
The Walsh group next applied their coupling platform to enantioselective sulfenate arylation (Scheme [9]).[28] Among the 192 ligands screened, notable enantioselectivity was observed with four, all of which were Josiphos-type ligands. Interestingly, the best ligand identified was Josiphos 6, which was also used by Madec and Poli in 2007.[27] The reaction conditions were compatible with a range of functional groups, such as amide, ketone, and tertiary amine (24 examples, 73–98% yield, 70–95% ee). Pharmaceutically relevant heterocycles, including pyridine and quinoline moieties, could also be incorporated into the sulfoxide structures. To illustrate the utility of the method, Walsh demonstrated the synthesis of diheteroaryl sulfoxides with high enantioselectivity. Moreover, the enantioselective coupling of benzene sulfenate, derived from sulfoxide 9, with pentadeuterobromobenzene (10) was achieved. Note that the enantioenriched sulfoxide product 11 would be extremely challenging to prepare by enantioselective oxidation of the corresponding sulfide.
As an alternative sulfenate precursor for arylation chemistry, Perrio and co-workers used tert-butyl sulfoxides of type H, first reported by the Walsh group,[20] under Pd/Xantphos catalysis (Scheme [10]).[12] The scope of both the aryl sulfenate anions and aryl (pseudo)halides was broad (21 examples, 40–99% yield), though arylation of methyl and benzyl sulfenates proceeded in 40% and 19% yields, respectively.
In 2015, Walsh and co-workers employed β-TMS ethyl sulfoxides of type B as versatile sulfenate precursors, especially for alkyl sulfenate generation, in Pd-catalyzed arylation reactions (Scheme [11]).[29] Sulfoxide B was originally introduced by Perrio as a precursor of sulfenate anions in 2007.[14] The use of sulfoxides of type B was effective in coupling benzyl, phenethyl, and alkyl (primary, secondary, and tertiary) sulfenate anions with an aryl bromide using a Pd/SPhos catalytic system (35 examples, 40–99% yield). The reactions demonstrated excellent functional group tolerance, where aryl bromides with ketone, secondary amide, aniline, and phenol groups proved to be viable. Importantly, this catalytic system was also applicable to aryl chlorides with both electron-rich and electron-deficient substituents. Walsh also demonstrated the use of sulfoxide 12 as an ‘SO’ donor, leveraging two distinct conditions for sulfenate anion generation. In the first step, fluoride-induced sulfenate formation followed by Pd-catalyzed arylation yielded the monoarylated product 13. This sulfoxide was subjected to alkoxide-induced sulfenate formation and subsequent Pd-catalyzed arylation to deliver the diarylated product 14. This synthesis illustrates the potential of sulfoxide 12 as an ‘SO’ donating reagent for synthesizing a diverse range of diaryl sulfoxides. Following the extension of this chemistry to the arylation of aryl sulfenates,[30] the Walsh group later utilized sulfoxides of type B for enantioselective alkenylation/arylation by applying a (Josiphos)Pd catalytic system.[31]
Among the methods reported to date, the most general approach for the enantioselective arylation of sulfenate anions was reported by Zhang and co-workers in 2018.[32] They employed a novel xanthene-based ligand, PC-Phos 15, featuring a sulfinamide group in the structure (Scheme [12]). This bidentate ligand coordinates to palladium via the P of the phosphine and the O of the sulfinamide. Zhang demonstrated the generality of the reaction by preparing a vast array of alkyl aryl sulfoxides and diaryl sulfoxides in high yields with excellent enantioselectivities (>100 examples, 45–98% yield, 86–99% ee). Many sensitive functional groups were well tolerated, such as aldehyde, ketone, and nitro groups, as well as nitrogen-containing heterocyclic structures, including quinoline and benzoxazole.
# 5
Coupling of Sulfenate Anions with Hypervalent Iodine Reagents
Transition-metal-free cross-coupling is a highly sought-after class of synthetic transformations because transition metals are costly, often require specialized ligands to achieve desired reactivity and selectivity, and residual metals are problematic in some products, such as pharmaceuticals and organic electronic materials. In this context, hypervalent iodine reagents have emerged as valuable tools for facilitating various bond-forming processes,[33] including carbon–sulfur bond formation. For instance, thiolates (RS–) and sulfinates (RSO2 –) can undergo coupling with hypervalent iodine reagents, leading to the formation of sulfides[34] and sulfones,[35] respectively.
In 2018, Bolm and co-workers reported that sulfenate anions also participated in similar coupling reactions with diaryliodonium salts (Scheme [13]).[36] The method was operationally simple, conducted at room temperature under biphasic conditions, and produced a significant number of aryl sulfoxides, mostly in high yields (26 examples, 19–98% yield). In the following year, Zhang and co-workers presented a conceptually similar reaction in non-aqueous settings, demonstrating the synthesis of aryl sulfoxides (33 examples, 62–91% yield).[37] However, in both cases, examples of aryl sulfenates with electron-withdrawing groups were limited to those substituted with chlorine (Cl) or bromine (Br). It remains unknown whether other electron-deficient aryl sulfenates can undergo the carbon–sulfur bond-forming coupling with diaryliodonium reagents.
In 2019, Waser and co-workers documented the transition-metal-free alkynylation and alkenylation of sulfenate anions with hypervalent iodine reagents (Scheme [14]).[38] They employed ethynyl benziodoxolone (EBX) reagents to convert in situ generated sulfenates into alkynyl sulfoxides (17 examples, 37–91% yield). Interestingly, the reaction proved to be sensitive to the terminal substituent on the alkyne. When the alkyne was capped with either a C14H29 or phenyl group, the desired sulfoxides were not obtained. Waser also demonstrated the facile removal of the terminal silyl protecting group (TIPS) with KF to reveal the free alkyne. This alkynylation chemistry is particularly intriguing since no example of the transition-metal-catalyzed alkynylation of sulfenate anions has been previously reported. As additional examples, the alkenylation of sulfenate anions was performed using vinyl benziodoxolone (VBX) reagents to yield alkenyl sulfoxides 16 and 17 in 52% and 25% yields, respectively.
# 6
Conclusions and Outlook
This review highlights recent developments on the synthesis of sulfoxides involving sulfenate anions as key intermediates, particularly focusing on organocatalytic enantioselective alkylation, palladium-catalyzed arylation, and transition-metal-free C–S bond formation with hypervalent iodine reagents. Among these processes, palladium-catalyzed coupling chemistry has flourished over the last 20 years, and a diverse array of sulfoxides can now be prepared in a highly enantioenriched manner using sulfenate protocols.
The synthetic chemistry of sulfenate anions is continuing to grow and advances are expected in the following areas:
(i) Metal-free coupling with aryl halides using light. Thiolates and sulfinates can form electron donor-acceptor (EDA) complexes with aryl halides. Upon photoirradiation, the complexes participate in the formation of radical pairs via charge transfer, followed by radical coupling to forge a C–S bond, thus affording sulfides[39] and sulfones.[40] Similarly, thianthrenium salts also form EDA complexes with thiolates and sulfinates to allow for late-stage sulfenylation[41] and sulfonylation[42] of pharmaceutically relevant molecules. These precedents indicate that sulfenate anions may also undergo similar metal-free couplings with aryl halides.
(ii) Enantioselective alkylation of alkyl sulfenates. Despite the versatility of Tan’s protocol,[23] enantioselective alkylation chemistry presents a large scope for further investigations. In particular, a general solution for the enantioselective alkylation of alkyl sulfenates is still lacking. It would also be desirable to enable enantioselective alkylation of sulfenate anions with a readily prepared catalyst, since the pentanidium catalyst 5 requires six steps for its preparation.
(iii) Alkylation with non-activated alkyl electrophiles. The alkylation of sulfenate anions always relies on simple nucleophilic substitution chemistry with reactive alkyl electrophiles (e.g., benzyl bromides and primary alkyl iodides). Thus, coupling with non-activated alkyl bromides, possibly through the use of transition-metal catalysis, would greatly expand the scope of alkyl sulfoxides accessible from sulfenate anions.
(iv) New methods for sulfenate formation. Sulfenate anions are usually generated from the designed sulfoxides (see Figure [1]). A drawback of this approach is that only one of the two substituents of a sulfoxide can be introduced through a C–S bond-forming event. To allow for two-fold C–S bond formation in one pot (or in one step), Saito recently disclosed the use of a sulfoxide reagent as a sulfur monoxide equivalent.[43] The sulfoxide donates an ‘SO’ group upon Grignard reaction (RMgX) and releases a sulfenate anion (RSO–), the trapping of which with carbon electrophiles results in the formation of sulfoxides. Though a variety of sulfenates can be accessed through this protocol, there are several limitations, such as the use of reactive organometallic nucleophiles and competitive side reactions including a sulfoxide/magnesium exchange process. A novel ‘SO’-donating reagent is still in demand, which would ideally produce sulfenate anions with mild and readily available nucleophiles (e.g., boronic acids).
The field of sulfenate anion chemistry in synthesis is still in its infancy. Further research efforts aimed at making sulfenate protocols more practical and broader in scope will transform the way chemists synthesize their target sulfoxides.
#
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Conflict of Interest
The author declares no conflict of interest.
Acknowledgment
The author is grateful to Prof. Oliver Trapp (Ludwig-Maximilians-Universität München) for his continuous support.
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Corresponding Author
Publication History
Received: 18 July 2023
Accepted after revision: 16 August 2023
Accepted Manuscript online:
16 August 2023
Article published online:
27 September 2023
© 2023. Thieme. All rights reserved
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References
- 1 Scott KA, Njardarson JT. Top. Curr. Chem. 2018; 376: 5
- 2a Jia T, Cao P, Wang B, Lou Y, Yin X, Wang M, Liao J. J. Am. Chem. Soc. 2015; 137: 13760
- 2b Yuan C.-H, Wang X.-X, Jiao L. Angew. Chem. Int. Ed. 2023; 62: e202300854
- 3a Kosugi H, Konta H, Uda H. J. Chem. Soc., Chem. Commun. 1985; 211
- 3b Solladié G, Demailly G, Greck C. Tetrahedron Lett. 1985; 26: 435
- 4a Pitchen P, Dunach E, Deshmukh MN, Kagan HB. J. Am. Chem. Soc. 1984; 106: 8188
- 4b Di Furia F, Modena G, Seraglia R. Synthesis 1984; 325
- 5 Egami H, Katsuki T. J. Am. Chem. Soc. 2007; 129: 8940
- 6a Andersen KK. Tetrahedron Lett. 1962; 3: 93
- 6b Andersen KK, Gaffield W, Papanikolaou NE, Foley JW, Perkins RI. J. Am. Chem. Soc. 1964; 86: 5637
- 7a Furukawa N, Konno Y, Tsuruoka M, Ogawa S. Heteroat. Chem. 1992; 3: 495
- 7b Refvik MD, Froese RD. J, Goddard JD, Pham HH, Pippert MF, Schwan AL. J. Am. Chem. Soc. 1995; 117: 184
- 7c Sandrinelli F, Perrio S, Beslin P. J. Org. Chem. 1997; 62: 8626
- 8 Riddell AB, Smith MR. A, Schwan AL. J. Sulfur Chem. 2022; 43: 540
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