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Transforming Olefins into ?,?-Unsaturated Nitriles through Copper Catalysis.

ABSTRACT: 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.

SUBMITTER: Wu X

PROVIDER: S-EPMC6824592 | biostudies-literature | 2017 Sep

REPOSITORIES: biostudies-literature

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Transforming Olefins into γ,δ-Unsaturated Nitriles through Copper Catalysis.

Wu Xuesong X Riedel Jan J Dong Vy M VM

Angewandte Chemie (International ed. in English) 20170810 38

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 ...[more]

PMID: 28796438

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