Catalytic Hydroalkylation of Allenes. (13th November 2017)

• Record Type: Journal Article
• Authors: Lee, Mitchell; Nguyen, Mary; Brandt, Chance; Kaminsky, Werner; Lalic, Gojko
• Is Part Of: Angewandte Chemie. Volume 129:Number 49(2017)
• Page Start: 15909
• Page End: 15913
• Publication Date: 2017-11-13
• Subjects: Alkylierungen -- Allene -- Homogene Katalyse -- Kreuzkupplungen -- Kupfer; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201709144
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: We have developed a catalytic method for the hydroalkylation of allenes using alkyl triflates as electrophiles and silane as a hydride source. The reaction has an excellent substrate scope and is compatible with a wide range of functional groups, including esters, aryl halides, aryl boronic esters, sulfonamides, alkyl tosylates, and alkyl bromides. We found evidence for a reaction mechanism that involves unusual dinuclear copper ally complexes as catalytic intermediates. The unusual structure of these complexes provides a rationale for their unexpected reactivity.