Transforming Olefins into γ, δ‐Unsaturated Nitriles through Copper Catalysis. (10th August 2017)

• Record Type: Journal Article
• Authors: Wu, Xuesong; Riedel, Jan; Dong, Vy M.
• Is Part Of: Angewandte Chemie. Volume 129:Number 38(2017)
• Page Start: 11747
• Page End: 11751
• Publication Date: 2017-08-10
• Subjects: Alkene -- Alkylnitrile -- Kreuzkupplungen -- Kupfer -- Radikale; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201705859
• Languages: English
• ISSNs: 0044-8249

Abstract

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.