Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 38, Pages 11589-11593Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201705859
Keywords
alkenes; alkylnitriles; copper; cross-coupling; radicals
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Funding
- National Science Foundation [CHE-1465263]
- UC Irvine
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1465263] Funding Source: National Science Foundation
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We have developed a strategy to transform olefins into homoallylic nitriles through a mechanism that combines copper catalysis with alkyl nitrile radicals. The radicals are easily generated from alkyl nitriles in the presence of the mild oxidant di-tert-butyl peroxide. This cross-dehydrogenative coupling between simple olefins and alkylnitriles bears advantages over the conventional use of halides and toxic cyanide reagents. With this method, we showcase the facile synthesis of a flavoring agent, a natural product, and a polymer precursor from simple olefins.
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