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An Expedient Variant of Heck Reaction of Alkenyl Nonaflates: Homogeneous Ligand‐Free Palladium Catalysis at Room Temperature
Author(s) -
Vogel Michael A. K.,
Stark Christian B. W.,
Lyapkalo Ilya M.
Publication year - 2007
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.200600388
Subject(s) - chemistry , palladium , catalysis , heck reaction , reagent , ligand (biochemistry) , homogeneous , homogeneous catalysis , coupling reaction , combinatorial chemistry , organic chemistry , thermodynamics , biochemistry , physics , receptor
A mechanistic study on the ligand‐free room‐temperature Heck reaction of alkenyl nonafluorobutanesulfonates (nonaflates) is described. Kinetic data obtained from poisoning experiments, centrifugation and variation of catalyst loading consistently provide evidence for a homogeneous palladium catalysis unprecedented in Heck chemistry. The Heck reaction of alkenyl perfluorobutanesulfonates represents a remarkably robust, active and efficient catalytic system generally applicable to the coupling with a broad range of terminal olefins including non‐activated ones under ambient conditions. It features insensitivity towards atmospheric oxygen and moisture, furnishing uniformly high yields of the anticipated coupling products without the necessity to purify commercial reagents and solvents.