Palladium-Catalyzed Cross-Coupling Syntheses of Benzotriazolyl Enynes and a General Route to Enynyl Ketones and Alkynyl Ketones.

AlanR. Katritzky, Jiangchao Yao, Ming Qi

Index: J. Org. Chem. 62(23) , 8201-8204, (1997)

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Abstract

A new general route to conjugated enynyl ketones was developed based on a two-step procedure. First, palladium-catalyzed cross-coupling reactions of 1-(benzotriazol-1-yl)propargyl ethyl ether (3) and vinyl triflates or vinyl bromides afforded the key intermediates [1-(benzotriazol-1-yl)-1-enynyl]methyl ethyl ethers 5a-d in good yields. Then reactions of compounds 5 with primary halides gave intermediates 8, which were hydrolyzed by dilute acid to enynyl ketones 9a-g. Similar palladium-catalyzed coupling reactions of 3 with various aryl iodides followed by an analogous sequence afforded aryl-substituted propargyl ethers 12a-d and thence alkynyl ketones 13a,b.