@article{0ce8637c90714fffb388f86c13450f17,
title = "An efficient synthesis of 4-substituted coumarin derivatives via a palladium-catalyzed Suzuki cross-coupling reaction",
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.",
keywords = "Atropisomerism, Coumarins, Organotrifluoroborates, Suzuki cross-coupling",
author = "Trideep Rajale and Shikha Sharma and Stroud, {Daniel A.} and Unruh, {Daniel K.} and Emily Miaou and Kimberly Lai and Birney, {David M.}",
note = "Funding Information: This research was supported by the Robert A. Welch Foundation Grant D-1239 (T.R., S.S. and D.A.S.) and by the Welch Summer Scholars program for high school students interested in chemistry (E.M. and K.L.). We are grateful for the use of a 400 MHz MNR spectrometer made available through the NSF CRIF MU Grant CHE-1048553. We thank Sunil Kumar Paladugu and Professor Michael F. Mayer for the chiral HPLC analysis of 1d and Dr. Kazimierz Surowiec for the high-resolution mass spectrometry using the ORBITRAP instrument funded and supported by Texas Tech University , the Department of Chemistry and Biochemistry and the Office of the Vice President for Research. Publisher Copyright: {\textcopyright} 2014 Elsevier Ltd. All rights reserved.",
year = "2014",
month = dec,
day = "3",
doi = "10.1016/j.tetlet.2014.10.078",
language = "English",
volume = "55",
pages = "6627--6630",
journal = "Tetrahedron Letters",
issn = "0040-4039",
number = "49",
}