An Expedient Variant of Heck Reaction of Alkenyl Nonaflates: Homogeneous Ligand-Free Palladium Catalysis at Room Temperature

• Published in: Advanced synthesis & catalysis Vol. 349; no. 7; pp. 1019 - 1024
• Main Authors: Vogel, Michael A. K., Stark, Christian B. W., Lyapkalo, Ilya M.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 07.05.2007; WILEY‐VCH Verlag; Wiley
• Subjects: alkenyl nonaflates; catalyst poisoning; Chemistry; Chemistry, Applied; Chemistry, Organic; Heck reaction; homogeneous catalysis; kinetics; ligand-free catalysis; Physical Sciences; Science & Technology; ROUTE; PALLADACYCLES; COMPLEXES; Heck reaction; HETEROGENEOUS CATALYSIS; homogeneous catalysis; IMINE; COUPLING REACTIONS; CHEMISTRY; ligand-free catalysis; kinetics; alkenyl nonaflates; PRECURSORS; catalyst poisoning
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.200600388

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.