An efficient synthesis of 4-substituted coumarin derivatives via a palladium-catalyzed Suzuki cross-coupling reaction

Trideep Rajale, Shikha Sharma, Daniel A Stroud, Daniel K Unruh, Emily Miaou, Kimberly Lai, David Birney

Research output: Contribution to journalArticlepeer-review

Abstract

An efficient Pd-catalyzed Suzuki cross-coupling reaction of sterically crowded 4-chlorocoumarin deriva- tives with air- and moisture-stable potassium organotrifluoroborates is developed. This methodology has been used to generate a series of novel alkyl, aryl, and vinyl substituted coumarin derivatives in good to excellent yields. The twisted conformation of the vinyl groups in the X-ray crystal structures of (2-oxo-4- vinyl-2H-chromen-3-yl)methyl acetate (2) and (2-oxo-4-vinyl-2H-chromen-3-yl)methyl 2,2,2-trichloro- acetimidate (3), along with the atropisomerism of 3-(hydroxymethyl)-4-(2-methoxyphenyl)-2H-chro- men-2-one (1d), are evidence of the steric crowding in these adducts.
Original languageEnglish
Pages (from-to)6627-6630
JournalTetrahedron Lett.
StatePublished - Oct 18 2014

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