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Copper-catalyzed synthesis of thiazol-2-yl ethers from oxime acetates and xanthates under redox-neutral conditions

Author:
Zhu, Zhongzhi, Tang, Xiaodong, Cen, Jinghe, Li, Jianxiao, Wu, Wanqing, Jiang, Huanfeng
Source:
Chemical communications 2018 v.54 no.30 pp. 3767-3770
ISSN:
1364-548X
Subject:
acetates, additives, chemical reactions, copper, ethers, ketones, ligands, regioselectivity
Abstract:
A novel copper-catalyzed annulation of oxime acetates and xanthates for the synthesis of thiazol-2-yl ethers with remarkable regioselectivity has been developed. Various oxime acetates, whether derived from aryl ketones or alkyl ketones, or natural product cores are suitable for this conversion. Unique dihydrothiazoles were also obtained when both reaction sites were methine. Mechanistic studies indicated that imino copper(iii) intermediates were involved. In addition, this protocol proceeded under redox-neutral conditions and did not require additives or ligands.
Agid:
6174656