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Cross‐Electrophile Coupling of Vinyl Halides with Alkyl Halides
Author(s) -
Johnson Keywan A.,
Biswas Soumik,
Weix Daniel J.
Publication year - 2016
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.201601320
Subject(s) - halide , alkyl , aryl , catalysis , electrophile , chemistry , coupling reaction , polymer chemistry , coupling (piping) , organic chemistry , materials science , composite material
Abstract An improved method for the reductive coupling of aryl and vinyl bromides with alkyl halides that gave high yields for a variety of substrates at room temperature with a low (2.5 to 0.5 mol %) catalyst loading is presented. Under the optimized conditions, difficult substrates, such as unhindered alkenyl bromides, can be coupled to give the desired olefins with minimal diene formation and good stereoretention. These improved conditions also worked well for aryl bromides. For example, a gram‐scale reaction was demonstrated with 0.5 mol % catalyst loading, whereas reactions at 10 mol % catalyst loading completed in as little as 20 minutes. Finally, a low‐cost single‐component pre‐catalyst, (bpy)NiI 2 (bpy=2,2′‐bipyridine) that is both air‐ and moisture‐stable over a period of months was introduced.