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Pure Appl. Chem., 2011, Vol. 83, No. 3, pp. 633-644

Published online 2011-01-31

Rational design of novel ligands for environmentally benign cross-coupling reactions

Oleg M. Demchuk*, Katarzyna Kielar and K. Michał Pietrusiewicz

Department of Organic Chemistry, Maria Curie-Sklodowska University, 33 Gliniana St., 20-614, Lublin, Poland

Abstract: Transition-metal (TM) complexes of new phosphines, readily prepared by a straight-forward three-step modular synthesis, were successfully employed in difficult cross-coupling reactions conducted under mild conditions (water, “open-flask”, low temperature) that aspire to meet green chemistry criteria. High yielding catalyzed by bismuth or rhodium complexes oxidative arylation of naphthoquinone gave the key 2-arylnaphthoquinone intermediates for facile bismuth triflate-catalyzed Michael addition of secondary phosphine oxides. Subsequent O-methylation and reductions of the resulting products gave access to the target air-stable phosphine ligands in good overall yields (up to 60 %).