RSS-Feed abonnieren
DOI: 10.1055/a-1912-1029
Recent Progress in C(sp2)–C(sp2) Bond Formation Using Ligand Coupling on Sulfur(IV)
T.M. thanks JSPS KAKENHI Grant Number JP22K14686 for the foundation.
![](https://www.thieme-connect.de/media/synthesis/202223/lookinside/thumbnails/ss-2022-f0297-sr_10-1055_a-1912-1029-1.jpg)
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, sulfoxidePublikationsverlauf
Eingereicht: 21. Juni 2022
Angenommen nach Revision: 28. Juli 2022
Accepted Manuscript online:
28. Juli 2022
Artikel online veröffentlicht:
21. September 2022
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
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
- 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
- 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
For pioneering woks of ligand coupling on sulfur, see:
For recent woks of ligand coupling on sulfur other than C(sp2)–C(sp2) coupling, see: