Pd-catalyzed decarboxylative allylic coupling of acetates of Baylis–Hillman alcohols with propiolic acids: a highly regio- and stereoselective synthesis of 1,5-diarylpent-1-en-4-yne derivatives

Autor: Gnanakalai Shanmugavel, Parthasarathy Muthuraman, Satyanarayana Tummanapalli, Kee Wei Lee, Sanjeeva Kambampati, Dhanunjaya Naidu Vangapandu
Rok vydání: 2015
Předmět:
Zdroj: RSC Advances. 5:49392-49399
ISSN: 2046-2069
DOI: 10.1039/c5ra06168g
Popis: Pd-catalyzed decarboxylative allylic coupling of acetates of Baylis–Hillman alcohols with alkynyl carboxylic acids leading to the formation of an important class of 1,5-diarylpent-1-en-4-ynes in a highly regio- and stereoselective manner has been developed. Decarboxylative coupling happened via an exclusively SN2′ pathway. Acetates of the Baylis–Hillman alcohols derived from alkyl acrylates, ethyl vinyl ketone and phenyl vinyl sulfone provided exclusively (E)-1,5-diarylpent-1-en-4-ynes while the acetates of the Baylis–Hillman alcohols derived from acrylonitrile provided exclusively (Z)-1,5-diarylpent-1-en-4-ynes.
Databáze: OpenAIRE