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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 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.201708800
Subject(s) - aryl , alkyl , chemistry , silane , catalysis , lithium aluminium hydride , halide , steric effects , medicinal chemistry , hydride , ruthenium , organic chemistry , metal
Abstract 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.