Synlett 2018; 29(19): 2449-2455
DOI: 10.1055/s-0037-1610230
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© Georg Thieme Verlag Stuttgart · New York

Transition-Metal-Free, Visible-Light-Promoted C–S Cross-Coupling through Intermolecular Charge Transfer

Bin Liu
Department of Chemistry, Colorado State University, 301 West Pitkin Street, Fort Collins, CO 80523, USA   Email: garret.miyake@colostate.edu
,
Chern-Hooi Lim
Department of Chemistry, Colorado State University, 301 West Pitkin Street, Fort Collins, CO 80523, USA   Email: garret.miyake@colostate.edu
,
Department of Chemistry, Colorado State University, 301 West Pitkin Street, Fort Collins, CO 80523, USA   Email: garret.miyake@colostate.edu
› Author Affiliations
This work was supported by Colorado State University and the ­Advanced Research Projects Agency-Energy (DE-AR0000683). ­Research reported in this publication was supported by the National Institute of General Medical Sciences of the National Institutes of Health under Award Number R35GM119702. The content is solely the responsibility of the authors and does not necessarily represent the official views of the National Institutes of Health. C.-H.L is grateful for an NIH F32 Postdoctoral Fellowship (F32GM122392).
Further Information

Publication History

Received: 04 June 2018

Accepted after revision: 10 July 2018

Publication Date:
08 August 2018 (online)

Abstract

C–S cross-couplings are an important class of reactions ­applied across organic synthesis, materials science, and pharma­ceuticals. Several different methodologies have been developed to achieve this significant transformation. However, currently available synthetic procedures significantly rely on transition metals. This article describes historical developments in the field of transition-metal-catalyzed C–S cross-coupling reactions, the development of a visible-light-driven and catalyst-free approach to C–S bond formation, and future outlooks.

 
  • References

    • 1a Feng M. Tang B. Liang SH. Jiang X. Curr. Top. Med. Chem. (Sharjah, United Arab Emirates) 2016; 16: 1200
    • 1b Ilardi EA. Vitaku E. Njardarson JT. J. Med. Chem. 2014; 57: 2832
    • 2a Song S. Zhang Y. Yeerlan A. Zhu B. Liu J. Jiao N. Angew. Chem. Int. Ed. 2017; 56: 2487
    • 2b Chauhan P. Mahajan S. Enders D. Chem. Rev. 2014; 114: 8807
    • 2c Beletskaya IP. Ananikov VP. Chem. Rev. 2011; 111: 1596
    • 2d Hartwig JF. Acc. Chem. Res. 2008; 41: 1534
  • 3 Kosugi M. Shimizu T. Migita T. Chem. Lett. 1978; 7: 13
  • 4 Norris T. Leeman K. Org. Process Res. Dev. 2008; 12: 869
  • 5 Murata M. Buchwald SL. Tetrahedron 2004; 60: 7397
  • 6 Fernández-Rodríguez MA. Shen Q. Hartwig JF. J. Am. Chem. Soc. 2006; 128: 2180
  • 7 Fernández-Rodríguez MA. Shen Q. Hartwig JF. Chem. Eur. J. 2006; 12: 7782
  • 8 Cristau HJ. Chabaud B. Chêne A. Christol H. Synthesis 1981; 892
  • 9 Cristau HJ. Chabaud B. Labaudiniere R. Christol H. J. Org. Chem. 1986; 51: 875
  • 10 Suzuki H. Abe H. Osuka A. Chem. Lett. 1980; 9: 1363
  • 11 Kwong FY. Buchwald SL. Org. Lett. 2002; 4: 3517
  • 12 Wong Y.-C. Jayanth TT. Cheng C.-H. Org. Lett. 2006; 8: 5613
  • 13 Correa A. Carril M. Bolm C. Angew. Chem. Int. Ed. 2008; 47: 2880
  • 14 Timpa SD. Pell CJ. Ozerov OV. J. Am. Chem. Soc. 2014; 136: 14772
    • 15a Nicewicz DA. MacMillan DW. C. Science 2008; 322: 77
    • 15b Ischay MA. Anzovino ME. Du J. Yoon TP. J. Am. Chem. Soc. 2008; 130: 12886
    • 15c Narayanam JM. R. Tucker JW. Stephenson CR. J. J. Am. Chem. Soc. 2009; 131: 8756
  • 16 Wang X. Cuny GD. Noël T. Angew. Chem. Int. Ed. 2013; 52: 7860
  • 17 Oderinde MS. Frenette M. Robbins DW. Aquila B. Johannes JW. J. Am. Chem. Soc. 2016; 138: 1760
  • 18 Jouffroy M. Kelly CB. Molander GA. Org. Lett. 2016; 18: 876
  • 19 Jiang M. Li H. Yang H. Fu H. Angew. Chem. Int. Ed. 2017; 56: 874
  • 20 Bunnett JF. Creary X. J. Org. Chem. 1974; 39: 3173
    • 21a Uyeda C. Tan Y. Fu GC. Peters JC. J. Am. Chem. Soc. 2013; 135: 9548
    • 21b Johnson MW. Hannoun KI. Tan Y. Fu GC. Peters JC. Chem. Sci. 2016; 7: 4091
    • 22a Theriot JC. Lim C.-H. Yang H. Ryan MD. Musgrave CB. Miyake GM. Science 2016; 352: 1082
    • 22b Pearson RM. Lim C.-H. McCarthy BG. Musgrave CB. Miyake GM. J. Am. Chem. Soc. 2016; 138: 11399
    • 22c Du Y. Pearson RM. Lim C.-H. Sartor SM. Ryan MD. Yang H. Damrauer NH. Miyake GM. Chem. Eur. J. 2017; 23: 10962
  • 23 Liu B. Lim C.-H. Miyake GM. J. Am. Chem. Soc. 2017; 139: 13616

    • For reviews, see:
    • 24a Rosokha SV. Kochi JK. Acc. Chem. Res. 2008; 41: 641
    • 24b Lima CG. de S. Lima T. deM. Duarte M. Jurberg ID. Paixão MW. ACS Catal. 2016; 6: 1389

    • For examples of visible-light-induced EDA chemistry, see:
    • 24c Arceo E. Jurberg ID. Álvarez-Fernández A. Melchiorre P. Nat. Chem. 2013; 5: 750
    • 24d Beatty JW. Douglas JJ. Miller R. McAtee RC. Cole KP. Stephenson CR. J. Chem. 2016; 1: 456
    • 24e Deng Y. Wei X.-J. Wang H. Sun Y. Nöel T. Wang X. Angew. Chem. Int. Ed. 2017; 56: 832