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 M. Birney

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

An efficient Pd-catalyzed Suzuki cross-coupling reaction of sterically crowded 4-chlorocoumarin derivatives 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-trichloroacetimidate (3), along with the atropisomerism of 3-(hydroxymethyl)-4-(2-methoxyphenyl)-2H-chromen-2-one (1d), are evidence of the steric crowding in these adducts.

Original languageEnglish
Pages (from-to)6627-6630
Number of pages4
JournalTetrahedron Letters
Volume55
Issue number49
DOIs
StatePublished - Dec 3 2014

Keywords

  • Atropisomerism
  • Coumarins
  • Organotrifluoroborates
  • Suzuki cross-coupling

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