期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 141, 期 48, 页码 18970-18976出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b11915
关键词
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资金
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
- NSF of China [21772222, 21821002]
- S&TCSM of Shanghai [17JC1401200, 18JC1415600]
Synergistic use of electrochemistry and organometallic catalysis has emerged as a powerful tool for site-selective C-H functionalization, yet this type of transformation has thus far mainly been limited to arene C-H functionalization. Herein, we report the development of electrochemical vinylic C-H functionalization of acrylic acids with alkynes. In this reaction an iridium catalyst enables C-H/O-H functionalization for alkyne annulation, affording alpha-pyrones with good to excellent yields in an undivided cell. Preliminary mechanistic studies show that anodic oxidation is crucial for releasing the product and regeneration of an Ir(III) intermediate from a diene-Ir(I) complex, which is a coordinatively saturated, 18-electron complex. Importantly, common chemical oxidants such as Ag(I) or Cu(II) did not give significant amounts of the desired product in the absence of electrical current under otherwise identical conditions.
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