Easily Prepared Air‐ and Moisture‐Stable Pd–NHC (NHC=N‐Heterocyclic Carbene) Complexes: A Reliable, User‐Friendly, Highly Active Palladium Precatalyst for the Suzuki–Miyaura Reaction

作者：Christopher J. O’Brien, Eric Assen B. Kantchev, Cory Valente, Niloufar Hadei, Gregory Adam Chass, Alan J. Lough, Alan C. Hopkinson, Michael G. Organ · 发表于：Chemistry - A European Journal · 年份：2006 · DOI：10.1002/chem.200600251 · 被引用次数：832 · 研究领域：Catalytic Cross-Coupling Reactions、N-Heterocyclic Carbenes in Organic and Inorganic Chemistry、Synthetic Organic Chemistry Methods

The synthesis of NHC-PdCl(2)-3-chloropyridine (NHC=N-heterocyclic carbene) complexes from readily available starting materials in air is described. The 2,6-diisopropylphenyl derivative was found to be highly catalytically active in alkyl-alkyl Suzuki and Negishi cross-coupling reactions. The synthesis, ease-of-use, and activity of this complex are substantial improvements over in situ catalyst generation and all current Pd-NHC complexes. The utilization of complex 4 led to the development of a reliable, easily employed Suzuki-Miyama protocol. Employing various reaction conditions allowed a large array of hindered biaryl and drug-like heteroaromatic compounds to be synthesized without difficulty.