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Development of efficient catalytic arylation of aldehydes with thioether-imidazolinium carbene ligands


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Title: Development of efficient catalytic arylation of aldehydes with thioether-imidazolinium carbene ligands
Authors: Kuriyama, Masami
Issue Date: 1-Apr-2012
Publisher: Pharmaceutical Society of Japan / 日本薬学会
Citation: Chemical and Pharmaceutical Bulletin, 60(4), pp.419-428; 2012
Abstract: Effective methods of ligand design have been highly sought due to the significant roles of ligands in controlling metal catalyses. In particular, easy-to-handle ligands to realize high reaction efficacy, substrate tolerance, and environmental friendliness are desirable. Novel bidentate ligands containing N-heterocyclic carbene and thioether moieties were developed based on findings of hemilabile coordination, whose precursors were crystalline solids stable enough to handle and store in the air. The thioether-imidazolinium carbene ligand successfully brought out high catalyst performance of palladium in the catalytic arylation of aldehydes with organoboron reagents, which tolerated a diverse range of substrates including poorly reactive, sterically hindered, and heterocyclic compounds. This process was applied to gram-scale synthesis using only water as solvent with high efficiency and also achieved the effective one-pot synthesis of 3-arylphthalides known as useful biologically active agents and important synthetic intermediates for naturally occurring compounds.
Keywords: Arylation / Hemilabile ligand / N-heterocyclic carbene / Organoboron reagent / Palladium / Thioether
URI: http://hdl.handle.net/10069/29081
ISSN: 00092363
DOI: 10.1248/cpb.60.419
Rights: © 2012 The Pharmaceutical Society of Japan.
Type: Journal Article
Text Version: publisher
Appears in Collections:Articles in academic journal

Citable URI : http://hdl.handle.net/10069/29081

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