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, A. Polyzos

Research output: Contribution to journalArticleResearchpeer-review

3 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1543-1551
Number of pages9
JournalOrganic and Biomolecular Chemistry
Volume16
Issue number9
DOIs
Publication statusPublished - 7 Mar 2018

Cite this

Czyz, M. L., Weragoda, G. K., Monaghan, R., Connell, T. U., Brzozowski, M., Scully, A. D., ... Polyzos, A. (2018). A visible-light photocatalytic thiolation of aryl, heteroaryl and vinyl iodides. Organic and Biomolecular Chemistry, 16(9), 1543-1551. https://doi.org/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. / A visible-light photocatalytic thiolation of aryl, heteroaryl and vinyl iodides. In: Organic and Biomolecular Chemistry. 2018 ; Vol. 16, No. 9. pp. 1543-1551.
@article{8e8bfa3030dc466b96b43f51eb26d161,
title = "A visible-light photocatalytic thiolation of aryl, heteroaryl and vinyl iodides",
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.",
author = "Czyz, {M. L.} and Weragoda, {G. K.} and R. Monaghan and Connell, {T. U.} and M. Brzozowski and Scully, {A. D.} and J. Burton and Lupton, {D. W.} and A. Polyzos",
year = "2018",
month = "3",
day = "7",
doi = "10.1039/c8ob00238j",
language = "English",
volume = "16",
pages = "1543--1551",
journal = "Organic and Biomolecular Chemistry",
issn = "1477-0520",
publisher = "The Royal Society of Chemistry",
number = "9",

}

Czyz, ML, Weragoda, GK, Monaghan, R, Connell, TU, Brzozowski, M, Scully, AD, Burton, J, Lupton, DW & 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. https://doi.org/10.1039/c8ob00238j

A visible-light photocatalytic thiolation of aryl, heteroaryl and vinyl iodides. / Czyz, M. L.; Weragoda, G. K.; Monaghan, R.; Connell, T. U.; Brzozowski, M.; Scully, A. D.; Burton, J.; Lupton, D. W.; Polyzos, A.

In: Organic and Biomolecular Chemistry, Vol. 16, No. 9, 07.03.2018, p. 1543-1551.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - A visible-light photocatalytic thiolation of aryl, heteroaryl and vinyl iodides

AU - Czyz, M. L.

AU - Weragoda, G. K.

AU - Monaghan, R.

AU - Connell, T. U.

AU - Brzozowski, M.

AU - Scully, A. D.

AU - Burton, J.

AU - Lupton, D. W.

AU - Polyzos, A.

PY - 2018/3/7

Y1 - 2018/3/7

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85042719859&partnerID=8YFLogxK

U2 - 10.1039/c8ob00238j

DO - 10.1039/c8ob00238j

M3 - Article

VL - 16

SP - 1543

EP - 1551

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 9

ER -

Czyz ML, Weragoda GK, Monaghan R, Connell TU, Brzozowski M, Scully AD et al. A visible-light photocatalytic thiolation of aryl, heteroaryl and vinyl iodides. Organic and Biomolecular Chemistry. 2018 Mar 7;16(9):1543-1551. https://doi.org/10.1039/c8ob00238j