@article{868a7795a6e84de8bcebac639092a5ef,
title = "Highly stereoselective palladium-catalyzed coupling reactions of captodative olefins acetylvinyl arenecarboxylates",
abstract = "The palladium-catalyzed reaction of the captodative olefin 3-(p-nitrobenzoyloxy)-3-buten-2-one (1a) with aryl and vinyl halides gave coupled products 4-aryl-and 4-vinyl-3-(p-nitrobenzoyloxy)-3-buten-2-ones, 4 and 6 respectively, with high Z stereoselection. (Ph3P)2PdCl2 also catalyzed cross-coupling alkylation, phenylation and vinylation with trialkylorganostannanes and bromo olefin (Z)-4-bromo-3-(p-nitrobenzoyloxy)-3-buten-2-one (2), providing the corresponding trisubstituted alkenes. For the preparation of n-butyl substituted derivative (Z)-3-(p-nitrobenzoyloxy)-3-octen-2-one (8b), the transmetallation with n-BuZnCl was a more efficient method. Retention of the Z configuration of 2 was in all cases maintained.",
keywords = "Arylation, Coupling reactions, Olefins, Organostannanes, Palladium, Tin, Zinc",
author = "Lourdes Villar and Bullock, {Joseph P.} and Khan, {Matheen M.} and Arumugam Nagarajan and Bates, {Roderick W.} and Bott, {Simon G.} and Gerardo Zepeda and Francisco Delgado and Joaquin Tamariz",
note = "Funding Information: We are grateful to Professor Everett J. Felker for reviewing the manuscript. We thank F. Labarrios for his help in spectroscopic measurements. We also thank Dr. Maria de Jesfis Rosales for useful X-ray comments. J.T. acknowledges financial support from DEPI/IPN (Grant 921769). L.V. thanks Depto. de Preparatoria Agrfcola, Universidad Aut6noma de Chapingo for the facilities provided. R.W.B. acknowledges the Robert A. Welch Foundation for financial support. S.G.B. is grateful to the Robert A. Welch Foundation and the UNT Research Office for financial support. A.N. thanks CONACYT",
year = "1996",
month = jun,
day = "28",
doi = "10.1016/0022-328X(96)06112-8",
language = "Ingl{\'e}s",
volume = "517",
pages = "9--17",
journal = "Journal of Organometallic Chemistry",
issn = "0022-328X",
number = "1-2",
}