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

Czyz, M, Weragoda, G, Monaghan, R, Connell, T, Brzozowski, M, Scully, A, Burton, J, Lupton, D and Polyzos, A 2018, 'A visible-light photocatalytic thiolation of aryl, heteroaryl and vinyl iodides', Organic and Biomolecular Chemistry, vol. 16, no. 9, pp. 1543-1551.


Document type: Journal Article
Collection: Journal Articles

Title A visible-light photocatalytic thiolation of aryl, heteroaryl and vinyl iodides
Author(s) Czyz, M
Weragoda, G
Monaghan, R
Connell, T
Brzozowski, M
Scully, A
Burton, J
Lupton, D
Polyzos, A
Year 2018
Journal name Organic and Biomolecular Chemistry
Volume number 16
Issue number 9
Start page 1543
End page 1551
Total pages 9
Publisher Royal Society of Chemistry
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.
Subject Medicinal and Biomolecular Chemistry not elsewhere classified
Keyword(s) Cross-Coupling Reactions
Sulfur Bond Formation
C-S
Photoredox Catalysis
Room-Temperature
Nickel-Catalyst
Thiyl Radicals
Z-Alkenes
Thiols
Complexes
DOI - identifier 10.1039/c8ob00238j
Copyright notice This journal is © The Royal Society of Chemistry 2018
ISSN 1477-0520
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