Synthesis of Amides by Mild Palladium-Catalyzed Aminocarbonylation of Arylsilanes with Amines Enabled by Copper(II) Fluoride

A general Pd-catalyzed synthesis of amides by oxidative aminocarbonylation of arylsilanes under mild conditions was accomplished for the first time. The reaction is promoted by a commercially available copper­(II) fluoride, which acts as a dual silane activator and mild oxidant, enabling highly effi...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-01, Vol.84 (1), p.338-345
Main Authors: Zhang, Jin, Hou, Yanyan, Ma, Yangmin, Szostak, Michal
Format: Article
Language:English
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Summary:A general Pd-catalyzed synthesis of amides by oxidative aminocarbonylation of arylsilanes under mild conditions was accomplished for the first time. The reaction is promoted by a commercially available copper­(II) fluoride, which acts as a dual silane activator and mild oxidant, enabling highly efficient aminocarbonylation of versatile arylsilanes at atmospheric CO pressure. The reaction is tolerant of a wide range of arylsilanes and various sensitive halide functional groups as well as a broad scope of amines are compatible with this oxidative process using cheap CO. A significant aspect involves the increased efficiency by the catalyst system. The reaction represents a segue into the powerful Pd-catalyzed oxidative transformations of organosilanes.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b02874