A Platform for the Synthesis of Diverse Phosphonyl and Thiofunctionalized Sulfoxonium Ylides

A practical strategy for the construction of diverse phosphonyl and thiofunctionalized sulfoxonium ylides via controllable monofunctionalization of hybrid I(III)/S(VI) ylides is presented. This process allows efficient P–H insertion of I(III)/S(VI) ylides under Cu catalysis, enabling the synthesis o...

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Bibliographic Details
Published in:Organic letters 2024-07, Vol.26 (27), p.5811-5816
Main Authors: Zou, Wen-Xuan, Hu, Qiong, Shen, Dan-Ting, Wu, Wen-Rong, Wei, Jiaohang, Yang, Zi-Feng, Bao, Mei-Zhu, Liu, Xiang, Zhang, Shang-Shi
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Language:English
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Summary:A practical strategy for the construction of diverse phosphonyl and thiofunctionalized sulfoxonium ylides via controllable monofunctionalization of hybrid I(III)/S(VI) ylides is presented. This process allows efficient P–H insertion of I(III)/S(VI) ylides under Cu catalysis, enabling the synthesis of phosphonyl sulfoxonium ylides, whereas reaction with sulfur-containing reagents including AgSCF3, KSC­(S)­OR, and KSCN under mild conditions resulted in α-trifluoromethylthiolation, dithiocarbanation, and thiocyanation of sulfoxonium ylides accordingly. Of note, wide substrate compatibility (108 examples), excellent efficiency (up to 99% yield), gram-scale experiments, and various product derivatizations highlight the synthetic utility of this protocol.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c02000