期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 20, 页码 5867-5870出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201801814
关键词
alcohols; carbonylation; copper; hydrides; hydroformylation
资金
- NSF [CHE-1664632]
We have developed a reductive carbonylation method by which unactivated alkyl iodides can be hydroxy-methylated to provide one-carbon-extended alcohol products under Cu-catalyzed conditions. The method is tolerant of alkyl b-hydrogen atoms, is robust towards a wide variety of functional groups, and was applied to primary, secondary, and tertiary alkyl iodide substrates. Mechanistic experiments indicate that the transformation proceeds by atom-transfer carbonylation (ATC) of the alkyl iodide followed in tandem by two CuH-mediated reductions in rapid succession. This radical mechanism renders the Cu-catalyzed system complementary to precious-metal-catalyzed reductive carbonylation reactions.
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