Premium
Cobalt‐Catalyzed Reductive Cross‐Coupling Between Styryl and Benzyl Halides
Author(s) -
Cai Yingxiao,
Benischke Andreas D.,
Knochel Paul,
Gosmini Corinne
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201603832
Subject(s) - halide , catalysis , chemistry , acetonitrile , stereospecificity , cobalt , coupling reaction , transition metal , reductive elimination , combinatorial chemistry , medicinal chemistry , photochemistry , polymer chemistry , organic chemistry
A simple and efficient protocol for the direct reductive cross‐coupling between alkenyl and benzyl halides using a Co/Mn system has been developed. This reaction proceeds smoothly in the presence of [CoBr 2 (PPh 3 ) 2 ] as the catalyst, with NaI as an additive in acetonitrile with a broad scope of functionalized alkenyl and benzyl halides. Different functional groups are tolerated on both coupling partners, thus, significantly extending the general scope of transition‐metal‐catalyzed benzylation of alkenyl halides. Moderate to excellent yields were also obtained. From a mechanistic point of view, a radical chain mechanism was proposed. This reaction is stereospecific and some studies suggest the retention of the double‐bond configuration.