Bifunctionalization of α‑Bromophenone: An Access to Functionalized β‑Keto Thiosulfones

A simple and high-yielding strategy to produce a variety of β-keto sulfides using asymmetrical and symmetrical thiosulfonates with ketones under mild conditions is reported. It was found that the various substituted compounds, with both electron-withdrawing and electron-donating substituents, afford...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-10, Vol.89 (19), p.14255-14264
Main Authors: Wen, Xiaoqing, Li, Mengxin, Peng, Xiaoyan, Liu, Chuanli, Zhong, Xianglin, Tan, Rui, Jiang, Hezhong, Li, Jiahong
Format: Article
Language:English
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Summary:A simple and high-yielding strategy to produce a variety of β-keto sulfides using asymmetrical and symmetrical thiosulfonates with ketones under mild conditions is reported. It was found that the various substituted compounds, with both electron-withdrawing and electron-donating substituents, afforded a wide range of β-keto thiosulfones (α-thioaryl-β-keto sulfones) in moderate to high yields. The transformations were reliable at the gram-scale, thus illustrating their efficiency and practicality. A plausible mechanism for the protocol is also proposed.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c01681