Chan-Lam-Type C-S Coupling Reaction by Sodium Aryl Sulfinates and Organoboron Compounds

Long Yin Lam; Cong Ma

doi:10.1021/acs.orglett.1c02299

Chan-Lam-Type C-S Coupling Reaction by Sodium Aryl Sulfinates and Organoboron Compounds

Long Yin Lam, Cong Ma

Research output: Journal article publication › Journal article › Academic research › peer-review

18 Citations (Scopus)

Abstract

A Chan-Lam-Type C-S coupling reaction using sodium aryl sulfinates has been developed to provide diaryl thioethers in up to 92% yields in the presence of a copper catalyst and potassium sulfite. Both electron-rich and electron-poor sodium aryl sulfinates and diverse organoboron compounds were tolerated for the synthesis of aryl and heteroaryl thioethers and dithioethers. The mechanistic study suggested that potassium sulfite was involved in the deoxygenation of sulfinate through a radical process.

Original language	English
Pages (from-to)	6164-6168
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	15
DOIs	https://doi.org/10.1021/acs.orglett.1c02299
Publication status	Published - 6 Aug 2021

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.1c02299

http://hdl.handle.net/10397/94011

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abstract = "A Chan-Lam-Type C-S coupling reaction using sodium aryl sulfinates has been developed to provide diaryl thioethers in up to 92% yields in the presence of a copper catalyst and potassium sulfite. Both electron-rich and electron-poor sodium aryl sulfinates and diverse organoboron compounds were tolerated for the synthesis of aryl and heteroaryl thioethers and dithioethers. The mechanistic study suggested that potassium sulfite was involved in the deoxygenation of sulfinate through a radical process. ",

author = "Lam, {Long Yin} and Cong Ma",

note = "Funding Information: We thank the funding support from the Research Grants Council of the Hong Kong Special Administrative Region, China (15100019 and C5008-19G); Hong Kong Polytechnic University internal grants (1-ZVPS, 1-ZE2E (Project of Strategic Importance), and a large equipment fund); and the State Key Laboratory of Chemical Biology and Drug Discovery. Publisher Copyright: {\textcopyright} 2021 American Chemical Society. All rights reserved.",

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AU - Ma, Cong

N1 - Funding Information: We thank the funding support from the Research Grants Council of the Hong Kong Special Administrative Region, China (15100019 and C5008-19G); Hong Kong Polytechnic University internal grants (1-ZVPS, 1-ZE2E (Project of Strategic Importance), and a large equipment fund); and the State Key Laboratory of Chemical Biology and Drug Discovery. Publisher Copyright: © 2021 American Chemical Society. All rights reserved.

PY - 2021/8/6

Y1 - 2021/8/6

N2 - A Chan-Lam-Type C-S coupling reaction using sodium aryl sulfinates has been developed to provide diaryl thioethers in up to 92% yields in the presence of a copper catalyst and potassium sulfite. Both electron-rich and electron-poor sodium aryl sulfinates and diverse organoboron compounds were tolerated for the synthesis of aryl and heteroaryl thioethers and dithioethers. The mechanistic study suggested that potassium sulfite was involved in the deoxygenation of sulfinate through a radical process.

AB - A Chan-Lam-Type C-S coupling reaction using sodium aryl sulfinates has been developed to provide diaryl thioethers in up to 92% yields in the presence of a copper catalyst and potassium sulfite. Both electron-rich and electron-poor sodium aryl sulfinates and diverse organoboron compounds were tolerated for the synthesis of aryl and heteroaryl thioethers and dithioethers. The mechanistic study suggested that potassium sulfite was involved in the deoxygenation of sulfinate through a radical process.

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Chan-Lam-Type C-S Coupling Reaction by Sodium Aryl Sulfinates and Organoboron Compounds

Abstract

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