Visible-Light-Driven Iodine-Catalyzed Synthesis of Unsymmetrical Disulfides via Oxidative Coupling

Abstract

Herein, a facile and environmentally friendly oxidative coupling reaction to obtain unsymmetrical disulfide compounds, without using metal or organic dyes as photocatalyst and only using a catalytic amount of iodine, was developed. Oxygen is used as oxidant in the reaction and the substrate scope is wide. A gram-scale synthesis also highlights the synthetic practicality of this photochemical strategy. Moreover, our mechanistic studies support the formation of disulfide products through free-radical coupling.

Key words

iodine - visible light - sulfur - coupling - unsymmetrical disulfides

• References

• 1a Kokotou MG, Revelou P.-K, Pappas C, Constantinou-Kokotou V. Food Chem. 2017; 237: 566
• 1b Mandal B, Basu B. RSC Adv. 2014; 4: 13854
• 1c Musiejuk M, Witt D. Org. Prep. Proced. Int. 2015; 47: 95
• 2a DiRaimondo TR, Plugis NM, Jin X, Khosla C. J. Med. Chem. 2013; 56: 1301
• 2b Vlahov IR, Santhapuram HK. R, Wang Y, Kleindl PJ, You F, Howard SJ, Westrick E, Reddy JA, Leamon CP. J. Org. Chem. 2007; 72: 5968
• 3a Kim S.-M, Jeon H, Shin S.-H, Park S.-A, Jegal J, Hwang SY, Oh DX, Park J. Adv. Mater. 2018; 30: 1705145
• 3b Cui HK, Guo Y, He Y, Wang FL, Chang HN, Wang YJ, Wu FM, Tian CL, Liu L. Angew. Chem. Int. Ed. 2013; 52: 9558
• 4 Neves RP. P, Fernandes PA, Ramos MJ. Proc. Natl. Acad. Sci. U. S. A. 2017; 114: E4724
• 5a Fass D, Thorpe C. Chem. Rev. 2018; 118: 1169
• 5b Kitson TM. J. Stud. Alcohol 1977; 38: 96
• 6 Kulkarni RA, Stanford SM, Vellore NA, Krishnamurthy D, Bliss MR, Baron R, Bottini N, Barrios AM. ChemMedChem 2013; 8: 1561
• 7a Ren S, Luo N, Liu K, Liu J.-B. J. Chem. Res. 2021; 45: 365
• 7b Yuan J, Liu C, Lei A. Org. Chem. Front. 2015; 2: 677
• 8 Stellenboom N, Hunter R, Caira MR. Tetrahedron 2010; 66: 3228
• 9a Parida A, Choudhuri K, Mal P. Chem. Asian J. 2019; 14: 2579
• 9b Mathuri A, Pramanik M, Parida A, Mal P. Org. Biomol. Chem. 2021; 19: 8539
• 10 Song L, Li W, Duan W, An J, Tang S, Li L, Yang G. Green Chem. 2019; 21: 1432
• 11 Huang P, Wang P, Tang S, Fu Z, Lei A. Angew. Chem. Int. Ed. 2018; 57: 8115
• 12 Oka M, Katsube D, Tsuji T, Iida H. Org. Lett. 2020; 22: 9244
• 13a Kushwaha AK, Maury SK, Kumari S, Kamal A, Singh HK, Kumar D, Singh S. Synthesis 2022; 54: 5099
• 13b Zeng JL, Wan J.-P, Liu Y. J. Org. Chem. 2022; 87: 13195
• 13c Patil DV, Hong YT, Kim HY, Oh K. Org. Lett. 2022; 24: 8465
• 13d Yu Q, Zhang Y, Wan J.-P. Green Chem. 2019; 21: 3436
• 14 Ren M.-Z, Yang Y.-H, Zhu Z.-H, Zhang B.-S, Quan Z.-J, Wang X.-C. Asian J. Org. Chem. 2021; 10: 1067
• 15a Fan W, Li Q, Li YR, Sun H, Jiang B, Li GG. Org. Lett. 2016; 18: 1258
• 15b Maejima S, Yamaguchi E, Itoh A. Adv. Synth. Catal. 2017; 359: 3883
• 15c Liao YF, Jiang PC, Chen SP, Qi HR, Deng GJ. Green Chem. 2013; 15: 3302
• 15d Yang FL, Wang FX, Wang TT, Wang YJ, Tian SK. Chem. Commun. 2014; 50: 2111
• 16 Vandavasi JK, Hu W.-P, Chen C.-Y, Wang J.-J. Tetrahedron 2011; 67: 8895
• 17 Han M, Lee JT, Hahn H.-G. Tetrahedron Lett. 2011; 52: 236
• 18 Hunter R, Caira M, Stellenboom N. J. Org. Chem. 2006; 71: 8268
• 19 Demkowicz S, Rachon J, Witt D. Synthesis 2008; 2033