Journal of Organic Chemistry 2009-02-06

Palladium-catalyzed decarboxylative coupling of alkynyl carboxylic acids and aryl halides.

Jeongju Moon, Mihee Jang, Sunwoo Lee

Index: J. Org. Chem. 74(3) , 1403-6, (2009)

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Abstract

2-Octynoic acid and phenylpropiolic acid were employed for the palladium-catalyzed decarboxylative coupling reaction and with a variety of aryl halides. The former needed 1,4-bis(diphenylphosphino)butane (dppb) as a ligand and the latter tri-tert-butylphosphine (P(t)Bu(3)), and both required 2 equiv of tetra-n-butylammonium fluoride (TBAF) for full conversion. These reactions showed high reactivities and tolerance of functional groups such as vinyl, ester, ether, ketone, and amine.