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Metal Complexes of N‐Heterocyclic Carbenes—A New Structural Principle for Catalysts in Homogeneous Catalysis

Angewandte Chemie International Edition in English · 1995 · Vol. 34(21) · pp. 2371–2374
Wolfgang A. HerrmannMartina ElisonJakob FischerChristian KöcherGeorg R. J. Artus

Abstract

Stabilized by “carbene” donor ligands, the Pd complex 1 catalyzes the Heck olefination of aryl halides unexpectedly efficiently and yet has long-term stability at elevated temperatures. The active Pd0 species can be generated during the Heck reaction or deliberately prepared by reduction of 1 with, for instance, hydrazine or sodium formate. Another similar catalyst can be synthesized in situ from Pd0 complexes and 1,3-dimethyldihydroimidazoline-2-ylidene.

Catalytic Cross-Coupling ReactionsN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCatalytic C–H Functionalization MethodsCatalysisCarbeneChemistrySodium formateHalideHydrazine (antidepressant)ArylHeck reactionFormateHomogeneous
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References
Principles and Applications of Organotransition Metal Chemistry
Journal of Organometallic Chemistry · 1987 · 2,140 citations
Water‐Soluble Ligands, Metal Complexes, and Catalysts: Synergism of Homogeneous and Heterogeneous Catalysis
Angewandte Chemie International Edition in English · 1993 · 738 citations
Palladacycles as Structurally Defined Catalysts for the Heck Olefination of Chloro‐ and Bromoarenes
Angewandte Chemie International Edition in English · 1995 · 816 citations
Fine Feathers Make Fine Birds: The Heck Reaction in Modern Garb
Angewandte Chemie International Edition in English · 1995 · 1,107 citations
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