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Short Paper | Regular issue | Vol 96, No. 10, 2018, pp.1795-1807
Published online, 23rd October, 2018
DOI: 10.3987/COM-18-13975
Palladium-Catalyzed One-Pot Approach to 3-(1,3-Diarylprop-2-yn-1-ylidene)oxindoles

Jiyun Lee, Sunhwa Park, Kye Jung Shin, and Jae Hong Seo*

*College of Pharmacy, The Catholic University of Korea, 43 Jinong-ro Wonmi-gu Bucheon, Gyeonggi-do, 420-743, Korea

Abstract

An efficient and stereoselective one-pot approach for synthesizing 3-(1,3-diarylprop-2-yn-1-ylidene)oxindoles has been developed, starting from propiolamide, aryl iodides and arylacetylenes and utilizing two palladium-catalyzed reactions: the Sonogashira and Heck reactions. This method produced (E)-3-(1,3-diarylprop-2-yn-1-ylidne)oxindoles as the major stereoisomers. This is the first time an effective synthetic method for (E)-isomer of these compounds has been reported.