Recent Progress in C(sp²)–C(sp²) Bond Formation Using Ligand Coupling on Sulfur(IV)

Abstract

Ligand coupling on sulfur, as an alternative to transition-metal-catalyzed cross-coupling reactions, is a useful method for connecting sp² carbons. Although pioneered more than 50 years ago, its synthetic utility has been overlooked until recently. This short review summarizes progress in C(sp²)–C(sp²) bond formation using ligand coupling on sulfur and discusses control of selectivity, expansion of the scope, and applications of the reaction.

1 Introduction

2 Cross-Coupling of Heteroaryl Reagents

3 Phenothiazinium-Mediated C(sp²)–C(sp²) Cross-Coupling

4 C(sp²)–C(sp²) Bond Formation Mediated by Sulfuranes Generated from Arynes and Sulfoxides

5 S-Alkenylbenzothiophenium-Mediated Alkenyl-Alkenyl Coupling

6 Conclusion

Key words

ligand coupling - sulfur - sulfurane - transition-metal-free - cross-coupling - sulfonium, sulfoxide

Publication History

Received: 21 June 2022

Accepted after revision: 28 July 2022

Accepted Manuscript online:
28 July 2022

Article published online:
21 September 2022

• References

• 1a Applied Cross-Coupling Reactions . Nishihara Y. Springer; Berlin: 2013
• 1b Metal-Catalyzed Cross-Coupling Reactions and More . de Meijere A, Bräse S, Oestreich M. Wiley-VCH; Weinheim: 2014
• 2a Hassan J, Sévignon M, Gozzi C, Schulz E, Lemaire M. Chem. Rev. 2002; 102: 1359
• 2b Johansson Seechurn CC. C, Kitching MO, Colacot TJ, Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062

For pioneering woks of ligand coupling on sulfur, see:
• 3a Ligand Coupling Reactions with Heteroatomic Compounds. In Tetrahedron Organic Chemistry Series, Vol. 18. Finnet J.-P. Pergamon; Oxford: 1998
• 3b Gilman H, Swayampati DR. J. Am. Chem. Soc. 1955; 77: 3387
• 3c Khim YH, Oae S. Bull. Chem. Soc. Jpn. 1969; 42: 1968
• 3d Trost B, LaRochelle R, Atkins R. J. Am. Chem. Soc. 1969; 91: 2175
• 3e LaRochelle RW, Trost BM. J. Am. Chem. Soc. 1971; 93: 6077
• 3f Hori M, Kataoka T, Shimizu H, Miyagaki M. Chem. Lett. 1972; 1: 515
• 3g Trost BM, Arndt HC. J. Am. Chem. Soc. 1973; 95: 5288
• 3h Oae S. Croat. Chem. Acta 1986; 59: 129
• 3i Oae S, Uchida Y. Acc. Chem. Res. 1991; 24: 202
• 3j Shibutani T, Fujihara H, Furukawa N. Tetrahedron Lett. 1991; 32: 2943
• 3k Baker RW, Sargent MV. Pure Appl. Chem. 1994; 66: 2143
• 3l Oae S, Ishihara H, Yoshihara M. Chem. Heterocycl. Compd. 1995; 31: 917
• 3m Baker RW, Hockless DC. R, Pocock GR, Sargent MV, Skelton BW, Sobolev AN, Twiss E, White AH. J. Chem. Soc., Perkin Trans. 1 1995; 2615
• 3n Sato S, Takahashi O, Furukawa N. Coord. Chem. Rev. 1998; 176: 483
• 3o Perry GJ. P, Yorimitsu H. ACS Sustainable Chem. Eng. 2022; 10: 2569

For recent woks of ligand coupling on sulfur other than C(sp²)–C(sp²) coupling, see:
• 4a Dean WM, Šiaučiulis M, Storr TE, Lewis W, Stockman RA. Angew. Chem. Int. Ed. 2016; 55: 10013
• 4b Morgan KF, Doran R, Croft RA, Hollingsworth IA, Bull JA. Synlett 2016; 27: 106
• 4c Selmani A, Schoenebeck F. Org. Lett. 2021; 23: 4779
• 5 Chemistry of Hypervalent Compounds . Akiba K.-y. Wiley-VCH; New York: 1998
• 6a Tian Z.-Y, Hu Y.-T, Teng H.-B, Zhang C.-P. Tetrahedron Lett. 2018; 59: 299
• 6b Kaiser D, Klose I, Oost R, Neuhaus J, Maulide N. Chem. Rev. 2019; 119: 8701
• 6c Berger F, Plutschack MB, Riegger J, Yu W, Speicher S, Ho M, Frank N, Ritter T. Nature 2019; 567: 223
• 6d Kafuta K, Korzun A, Böhm M, Golz C, Alcarazo M. Angew. Chem. Int. Ed. 2020; 59: 1950
• 6e Ma N.-N, Ren J.-A, Liu X, Chu X.-Q, Rao W, Shen Z.-L. Org. Lett. 2022; 24: 1953
• 7a Kawai T, Furukawa N, Oae S. Tetrahedron Lett. 1984; 25: 2549
• 7b Furukawa N, Shibutani T, Fujihara H. Tetrahedron Lett. 1987; 28: 5845
• 7c Oae S, Kawai T, Furukawa N. Phosphorus Sulfur Relat. Elem. 1987; 34: 123
• 7d Oae S, Takeda T, Wakabayashi S. Tetrahedron Lett. 1988; 29: 4445
• 7e Furukawa N, Shibutani T, Fujihara H. Tetrahedron Lett. 1989; 30: 7091
• 7f Uenishi J, Tanaka T, Wakabayashi S, Oae S, Tsukube H. Tetrahedron Lett. 1990; 31: 4625
• 7g Furukawa N, Ogawa S, Matsumura K, Fujihara H. J. Org. Chem. 1991; 56: 6341
• 7h Inubushi Y, Yoshihara M, Oae S. Heteroat. Chem. 1996; 7: 299
• 7i Oae S, Takeda T, Uenishi J, Wakabayashi S. Phosphorus, Sulfur Silicon Relat. Elem. 1996; 115: 179
• 8a Markovic T, Rocke BN, Blakemore DC, Mascitti V, Willis MC. Chem. Sci. 2017; 8: 4437
• 8b Markovic T, Murray PR. D, Rocke BN, Shavnya A, Blakemore DC, Willis MC. J. Am. Chem. Soc. 2018; 140: 15916
• 9 Zhou M, Tsien J, Qin T. Angew. Chem. Int. Ed. 2020; 59: 7372 ; corrigendum: Angew. Chem. Int. Ed. 2021, 60, 5601
• 10a Duong VK, Horan AM, McGarrigle EM. Org. Lett. 2020; 22: 8451
• 10b Horan AM, Duong VK, McGarrigle EM. Org. Lett. 2021; 23: 9089
• 11 Wei J, Liang H, Ni C, Sheng R, Hu J. Org. Lett. 2019; 21: 937
• 12 Baker RW, Rea SO, Sargent MV, Schenkelaars EM. C, Tjahjandarie TS, Totaro A. Tetrahedron 2005; 61: 3733
• 13a Morofuji T, Yoshida T, Tsutsumi R, Yamanaka M, Kano N. Chem. Commun. 2020; 56: 13995
• 13b Yoshida T, Honda Y, Morofuji T, Kano N. Org. Lett. 2021; 23: 9664
• 14 Yoshida T, Honda Y, Morofuji T, Kano N. J. Org. Chem. 2022; 87: 7565
• 15 Chen D.-L, Sun Y, Chen M, Li X, Zhang L, Huang X, Bai Y, Luo F, Peng B. Org. Lett. 2019; 21: 3986
• 16 Ritts CB, Hoye TR. J. Am. Chem. Soc. 2021; 143: 13501
• 17 Šiaučiulis M, Ahlsten N, Pulis AP, Procter DJ. Angew. Chem. Int. Ed. 2019; 58: 8779