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Catalytic Reduction of Alkyl and Aryl Bromides Using Propan‐2‐ol
Author(s) -
Haibach Michael C.,
Stoltz Brian M.,
Grubbs Robert H.
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201708800
Subject(s) - aryl , chemistry , alkyl , silane , catalysis , steric effects , lithium aluminium hydride , halide , ruthenium , medicinal chemistry , zincate , organic chemistry , hydride , zinc , metal
Milstein's complex, (PNN)RuHCl(CO), catalyzes the efficient reduction of aryl and alkyl halides under relatively mild conditions by using propan‐2‐ol and a base. Sterically hindered tertiary and neopentyl substrates are reduced efficiently, as well as more functionalized aryl and alkyl bromides. The reduction process is proposed to occur by radical abstraction/hydrodehalogenation steps at ruthenium. Our research represents a safer and more sustainable alternative to typical silane, lithium aluminium hydride, and tin‐based conditions for these reductions.