Visible-Light-Mediated Regioselective Chlorosulfonylation of Acrylamides

Abstract

A one-step chlorosulfonylation of acrylamides via a photocatalytic redox process is described. This reaction provides α-chlorosulfonylamides with a quaternary center with high regioselectivity via radical process. It is amenable to a broad range of substrates and the products are obtained in moderate to good yields.

Key words

acrylamides - difunctionalization of alkenes - photocatalysis - chlorosulfonylation - α-chlorosulfones

Publication History

Received: 30 November 2022

Accepted after revision: 30 January 2023

Article published online:
23 March 2023

• References

• 1a Glennon RA. J. Med. Chem. 2003; 46: 2795
• 1b Sikazwe D, Bondarev ML, Dukat M, Rangisetty JB, Roth BL, Glennon RA. J. Med. Chem. 2006; 49: 5217
• 1c Chen X, Parveen S, Zhang S, Yang Y, Zhu C. Curr. Med. Chem. 2012; 19: 3578
• 2 MacMillan KS, Naidoo J, Liang J, Melito L, Williams NS, Morlock L, Huntington PJ, Estill SJ, Longgood J, Becker GL, McKnight SL. J. Am. Chem. Soc. 2011; 133: 1428
• 3a Jorissen RN, Reddy GS. K. K, Ali A, Altman MD, Chellappan S, Anjum SG, Tidor B, Schiffer CA, Rana TM, Gilson MK. J. Med. Chem. 2009; 52: 737
• 3b Piscitelli F, Coluccia A, Brancale A, La Regina G, Sansone A, Giordano C, Balzarini J, Maga G, Zanoli S, Samuele A, Cirilli R, LaTorre F, Lavecchia A, Novellino E, Silvestri R. J. Med. Chem. 2009; 52: 1922
• 4 Chen X, Hussain S, Parveen S, Zhang S, Yang Y, Zhu C. Curr. Med. Chem. 2012; 19: 3578
• 5 Humljan J, Kotnik M, Contreras-Martel C, Blanot D, Urleb U, Dessen A, Solmajer T, Gobec S. J. Med. Chem. 2008; 51: 7486
• 6a Sato K, Hyodo M, Aoki M, Zheng XQ, Noyori R. Tetrahedron 2001; 57: 2469
• 6b Ruff F, Fábián A, Farkas Ö, Kucsman Á. Eur. J. Org. Chem. 2009; 2102
• 6c Kirihara M, Itou A, Noguchi T, Yamamoto J. Synlett 2010; 1557
• 6d Bahrami K, Khodaei MM, Arabi MS. J. Org. Chem. 2010; 75: 6208
• 6e Voutyritsa E, Trianda-fillidi I, Kokotos CG. Synthesis 2017; 48: 917
• 6f Wang Y, Jiang W, Huo C. J. Org. Chem. 2017; 82: 10628

Reviews on sulfone synthesis:
• 7a Liu N.-W, Liang S, Manolikakes G. Synthesis 2016; 48: 1939
• 7b Zhu C, Cai Y, Jiang H. Org. Chem. Front. 2021; 8: 5574
• 7c Zhang R, Ding H, Pu X, Qian Z, Xiao Y. Catalysts 2020; 10: 1339
• 7d Liang S, Hofman K, Friedrich M, Keller J, Manolikakes G. ChemSusChem 2021; 14: 4878
• 7e Fang Y, Luo Z, Xu X. RSC Adv. 2016; 6: 59661
• 8a Choudary BM, Chowdaria NS, Kantama ML. J. Chem. Soc., Perkin Trans. 1 2000; 2689
• 8b Nara SJ, Harjani JR, Salunkhe MM. J. Org. Chem. 2001; 66: 8616
• 9a Shyam PK, Jang HY. J. Org. Chem. 2017; 82: 1761
• 9b Liang S, Hofman K, Friedrich M, Manolikakes G. Eur. J. Org. Chem. 2020; 4664
• 10a Taniguchi N. Synlett 2011; 1308
• 10b Kumar M, Ahmed R, Singh M, Sharma S, Thatikonda T, Singh PP. J. Org. Chem. 2020; 85: 716
• 10c Shelke GM, Rao VK, Pericherla K, Kumar A. Synlett 2014; 25: 2345
• 10d Kadari L, Palakodety RK, Yallapragada LP. Org. Lett. 2017; 19: 2580
• 10e He F.-S, Gong Y, Rojsitthisak P, Wu J. J. Org. Chem. 2019; 84: 13159
• 10f Wang P.-L, Gao H, Jiang Z.-S, Li C, Tian Z.-H, Li P.-H. Synlett 2020; 31: 1720
• 11 Matviitsuk A, Panger JL, Denmark SE. Angew. Chem. Int. Ed. 2020; 59: 19796
• 12a Chaudhary R, Natarajan P. ChemistrySelect 2017; 2: 6458
• 12b Wallentin C.-J, Nguyen JD, Finkbeiner P, Stephenson CR. J. J. Am. Chem. Soc. 2012; 134: 8875
• 13 Niu T.-F, Lin D, Jiang D.-Y, Ni B.-Q. Synlett 2018; 29: 364
• 14 Xia P.-J, Liu F, Li S.-H, Xiao J.-A. Org. Chem. Front. 2022; 9: 709
• 15a Hossain A, Engl S, Lutsker E, Reiser O. ACS Catal. 2019; 9: 1103
• 15b Engl S, Reiser O. Eur. J. Org. Chem. 2020; 1523
• 16 Alkan Zambaba M, Hu X.-L. J. Org. Chem. 2019; 84: 4525
• 17 Zhang M, Ding X, Lu A, Kang J, Gao Y, Wang Z, Li H, Wang Q. Org. Chem. Front. 2021; 8: 961
• 18 Formentín P, Sabater MJ, Chrétien MN, García H, Scaiano JC. J. Chem. Soc., Perkin Trans. 2 2002; 164
• 19 Pertusati F, Ferla S, Bassetto M, Brancale A, Khandil S, Westwell AD, McGuigan C. Eur. J. Med. Chem. 2019; 180: 1
• 20 Wang K, Ding Z, Zhou Z, Kong W. J. Am. Chem. Soc. 2018; 140: 12364
• 21 Yi X, Lei S, Liu W, Che F, Yu C, Liu X, Wang Z, Zhou X, Zhang Y. Org. Lett. 2020; 22: 4583
• 22 Ni Z, Wang S, Huang X, Wang J, Pan Y. Tetrahedron 2015; 56: 2512
• 23 Huang B, Zhao Y, Yang C, Gao Y, Xia W. Org. Lett. 2017; 19: 3799
• 24 Zheng L, Huang H, Yang C, Xia W. Org. Lett. 2015; 17: 1034
• 25 Chen BC, Zhao R, Gove S, Wang B, Sundeen JE, Salvati ME, Barrish JC. J. Org. Chem. 2003; 68: 10181
• 26 Hegazya MA, ElHamouly SH, Azabb MM, Beshirc SI, Zayedc MA. Polym. Sci. Ser. B 2014; 56: 182
• 27 Cvetovich RJ, DiMichele L. Org. Process Res. Dev. 2006; 10: 944
• 28 Ackermann L, Lygin AV, Hofmann N. Org. Lett. 2011; 13: 3278