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Visible Light‐Driven, Room Temperature Heck‐Type Reaction of Alkyl Halides with Styrene Derivatives Catalyzed by B 12 Complex
Author(s) -
Chen Li,
Hisaeda Yoshio,
Shimakoshi Hisashi
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801707
Subject(s) - chemistry , alkyl , catalysis , heck reaction , halide , styrene , cobalt , photochemistry , coupling reaction , photosensitizer , visible spectrum , polymer chemistry , medicinal chemistry , organic chemistry , palladium , copolymer , polymer , physics , optoelectronics
A visible light driven Heck‐type coupling reaction of alkyl halides with styrene and its derivatives catalyzed by the cobalamin derivative (B 12 ) with the [Ru(bpy) 3 ]Cl 2 photosensitizer at room temperature is reported. The catalytic efficiencies of the B 12 catalyst were compared to that of other cobalt complexes such as cobaloxime. Various control experiments supported a radical‐based mechanism similar to those for typical B 12 model reactions. A unique coupling reaction combined with 1,2‐migration of the functional group is also reported. Mild reaction conditions using an environmentally benign cobalt catalyst derived from the natural B 12 provided a practical protocol for the synthetic organic chemistry of the B 12 catalyzed reaction system.