Premium
Aluminum Hydride Catalyzed Hydroboration of Alkynes
Author(s) -
Bismuto Alessandro,
Thomas Stephen P.,
Cowley Michael J.
Publication year - 2016
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.201609690
Subject(s) - hydroboration , hydride , catalysis , chemistry , aluminum hydride , organic chemistry , metal , methoxide
An aluminum‐catalyzed hydroboration of alkynes using either the commercially available aluminum hydride DIBAL‐H or bench‐stable Et 3 Al⋅DABCO as the catalyst and H‐Bpin as both the boron reagent and stoichiometric hydride source has been developed. Mechanistic studies revealed a unique mode of reactivity in which the reaction is proposed to proceed through hydroalumination and σ‐bond metathesis between the resultant alkenyl aluminum species and HBpin, which acts to drive turnover of the catalytic cycle.