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

Jin Zhang, Yanyan Hou, Yangmin Ma, Michal Szostak

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Abstract

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.

Original languageEnglish (US)
Pages (from-to)338-345
Number of pages8
JournalJournal of Organic Chemistry
Volume84
Issue number1
DOIs
Publication statusPublished - Jan 4 2019

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All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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