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Czyz ML, Weragoda GK, Monaghan R, et al. A visible-light photocatalytic thiolation of aryl, heteroaryl and vinyl iodides. Org Biomol Chem. 2018;16(9):1543-1551doi: 10.1039/c8ob00238j.
Czyz, M. L., Weragoda, G. K., Monaghan, R., Connell, T. U., Brzozowski, M., Scully, A. D., Burton, J., Lupton, D. W., & Polyzos, A. (2018). A visible-light photocatalytic thiolation of aryl, heteroaryl and vinyl iodides. Organic & biomolecular chemistry, 16(9), 1543-1551. https://doi.org/10.1039/c8ob00238j
Czyz, M L, et al. "A visible-light photocatalytic thiolation of aryl, heteroaryl and vinyl iodides." Organic & biomolecular chemistry vol. 16,9 (2018): 1543-1551. doi: https://doi.org/10.1039/c8ob00238j
Czyz ML, Weragoda GK, Monaghan R, Connell TU, Brzozowski M, Scully AD, Burton J, Lupton DW, Polyzos A. A visible-light photocatalytic thiolation of aryl, heteroaryl and vinyl iodides. Org Biomol Chem. 2018 Feb 28;16(9):1543-1551. doi: 10.1039/c8ob00238j. PMID: 29431836.
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Org Biomol Chem. 2018 Feb 28;16(9):1543-1551. doi: 10.1039/c8ob00238j.

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

Organic & biomolecular chemistry

M L Czyz, G K Weragoda, R Monaghan, T U Connell, M Brzozowski, A D Scully, J Burton, D W Lupton, A Polyzos

Affiliations

  1. CSIRO Manufacturing, Research Way, Clayton, VIC 3168, Australia. [email protected].

PMID: 29431836 DOI: 10.1039/c8ob00238j

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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