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Issue 9, 2018
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A visible-light photocatalytic thiolation of aryl, heteroaryl and vinyl iodides

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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.

Graphical abstract: A visible-light photocatalytic thiolation of aryl, heteroaryl and vinyl iodides

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Supplementary files

Article information


Submitted
03 Dec 2017
Accepted
31 Jan 2018
First published
12 Feb 2018

Org. Biomol. Chem., 2018,16, 1543-1551
Article type
Paper

A visible-light photocatalytic thiolation of aryl, heteroaryl and vinyl iodides

M. L. Czyz, G. K. Weragoda, R. Monaghan, T. U. Connell, M. Brzozowski, A. D. Scully, J. Burton, D. W. Lupton and A. Polyzos, Org. Biomol. Chem., 2018, 16, 1543
DOI: 10.1039/C8OB00238J

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