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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
Author(s) -
O'Brien Christopher J.,
Kantchev Eric Assen B.,
Valente Cory,
Hadei Niloufar,
Chass Gregory A.,
Lough Alan,
Hopkinson Alan C.,
Organ Michael G.
Publication year - 2006
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200600251
Subject(s) - carbene , alkyl , palladium , chemistry , combinatorial chemistry , catalysis , suzuki reaction , negishi coupling , derivative (finance) , organic chemistry , business , finance
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.