Rhodium-Catalyzed Cyclization of 1,6-Enynes Triggered by Addition of Arylboronic Acids

Abstract

1,6-Enynes reacted with arylboronic acids in the presence of a catalytic amount of a rhodium(I) complex under mild conditions to give (Z)-1-(1-arylethylidene)-2-vinylcyclopentanes. The regioselective addition of an arylrhodium(I) species across the carbon−carbon triple bond triggered the cyclization process. Intramolecular carborhodation onto the pendent alkene in a 5-exo mode furnished a five-membered ring. Finally, the rhodium(I) methoxide generated by β-methoxy elimination reacted with the arylboronic acid to promote the next catalytic cycle.