A visible-light photocatalytic thiolation of aryl, heteroaryl and vinyl iodides. Issue 9 (12th February 2018)

• Record Type: Journal Article
• Authors: Czyz, M. L.; Weragoda, G. K.; Monaghan, R.; Connell, T. U.; Brzozowski, M.; Scully, A. D.; Burton, J.; Lupton, D. W.; Polyzos, A.
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 9(2018)
• Page Start: 1543
• Page End: 1551
• Publication Date: 2018-02-12
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob00238j
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A method for the light-driven synthesis of aryl and vinyl alkyl thioethers from a range of C(sp 2 )–I bonds is reported. Abstract : The general catalytic synthesis of aryl and vinyl thioethers from readily available halides remains a challenge. Herein we report a unified method for the thiolation of aryl and vinyl iodides with dialkyl disulfides using visible light photoredox catalysis. A range of thioether products bearing diverse functional groups can be accessed in high yield and with excellent chemoselectivity. We demonstrate the versatility of this method through the expedient synthesis of a family of thioether-rich natural products. A detailed investigation of the photocatalytic mechanism is presented from both steady-state and time-resolved luminescent quenching as well as transient absorption spectroscopy experiments.