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Catalytic Hydroalkylation of Allenes
Author(s) -
Lee Mitchell,
Nguyen Mary,
Brandt Chance,
Kaminsky Werner,
Lalic Gojko
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201709144
Subject(s) - alkyl , aryl , chemistry , catalysis , electrophile , reactivity (psychology) , silane , substrate (aquarium) , combinatorial chemistry , reagent , organic chemistry , biology , medicine , ecology , alternative medicine , pathology
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.