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Synthesis and Catalytic Applications of [N,N]‐Pyrrole Ligands for the Regioselective Synthesis of Styrene Derivatives
Author(s) -
HochbergerRoa Frank,
CortésMendoza Salvador,
GallardoRosas David,
Toscano Ruben A.,
OrtegaAlfaro M. Carmen,
LópezCortés José G.
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.201900365
Subject(s) - chemistry , regioselectivity , styrene , ethylene , catalysis , palladium , aryl , acrylate , methyl acrylate , pyrrole , heck reaction , polymer chemistry , halide , combinatorial chemistry , medicinal chemistry , organic chemistry , copolymer , polymer , alkyl
We report the synthesis of two [N,N]‐donor ligands ( 5 a – b ) containing a 2‐chalcogenazoline as the structural motif. These compounds were synthesized from a common intermediate Fischer type aminocarbene complex ( 3 ). The palladium‐complexes of these [N,N]‐donor ligands were successfully used as catalytic precursors in the Mizoroki‐Heck coupling reaction between aryl halides and methyl acrylate, styrene and ethylene. For methyl acrylates, high yields with TOF values between 0.6 and 5.5×10 5 h −1 were obtained. In the case of ethylene, we reached high regioselectivities to obtain a diversity of styrene derivatives under soft pressure conditions, with good values of TON and TOF.