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Rhodium-Catalyzed Addition of Arylboronic Acids to Alkynyl Aza-Heteroaromatic Compounds in Water

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journal contribution
posted on 03.01.2003, 00:00 by Mark Lautens, Masahiro Yoshida
Alkynyl heteroaromatic compounds reacted with arylboronic acids to give addition products in the presence of a rhodium catalyst. The best results were obtained when a novel pyridine-substituted water-soluble phosphine ligand was used. The reactions proceed to give trisubstituted alkenes from various arylboronic acids and alkynyl heteroaromatic compounds with high regioselectivity. Only alkynes with a nitrogen atom in proximity to the triple bond were converted to the corresponding alkenes, as expected for a chelation-controlled addition.