Synthesis of 3-(Diarylmethylene)oxindoles via a Palladium-Catalyzed One-Pot Reaction: Sonogashira–Heck–Suzuki–Miyaura Combined Reaction

Dedicated with respect to Professor Deukjoon Kim on the occasion of his 65^th birthday

Abstract

A novel one-pot reaction for the synthesis of 3-(diarylmethylene)oxindoles is described. The reaction involves the successive combination of three palladium-catalyzed reactions (Sonogashira, Heck, and Suzuki–Miyaura reactions). This method enables the rapid synthesis of various 3-(diarylmethylene)oxindoles from simple propiolamides. The addition of silver salts dramatically enhanced the E/Z stereoselectivity of the reaction.

Key words

palladium - stereoselectivity - Heck reaction - ­Sonogashira reaction - oxindole

• References and Notes

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