Title |
A visible-light photocatalytic thiolation of aryl, heteroaryl and vinyl iodides
|
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Published in |
Organic and Biomolecular Chemistry, January 2018
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DOI | 10.1039/c8ob00238j |
Pubmed ID | |
Authors |
M. L. Czyz, G. K. Weragoda, R. Monaghan, T. U. Connell, M. Brzozowski, A. D. Scully, J. Burton, D. W. Lupton, A. Polyzos |
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. |
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