Journal
ACS CATALYSIS
Volume 9, Issue 8, Pages 6993-6998Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b02420
Keywords
protic NHC; N-Heterocyclic Carbene; ambidentate ligand; cross-coupling; green chemistry
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Funding
- North Carolina State University
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A family of air- and moisture-stable dinuclear palladium complexes bearing 2-benzimidazolyl ligands is reported and shown to be a highly effective and general catalytic platform in diverse cross-coupling reactions. The rigidity and conformation of the ligand scaffold was readily modified via tethering of the 2-benzimidazolyl moiety to diamine ligands, resulting in significant changes in catalytic activity. Under optimal conditions, Suzuki, Heck, and Sonogashira-type couplings of aryl bromides can all be performed efficiently with good functional group compatibility using only 0.1 mol % of catalyst, in aqueous or alcohol solvents. Experimental evidence highlights the importance of the bifunctional character of the ligand for catalytic activity, where the basic N-functionality in the ligand framework is proposed to accelerate (trans)metalation steps via intramolecular assistance.
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