Premium
Room‐Temperature, Ligand‐ and Base‐Free Heck Reactions of Aryl Diazonium Salts at Low Palladium Loading: Sustainable Preparation of Substituted Stilbene Derivatives
Author(s) -
Felpin FrançoisXavier,
Miqueu Karinne,
Sotiropoulos JeanMarc,
Fouquet Eric,
Ibarguren Oier,
Laudien Julia
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200903050
Subject(s) - chemistry , aryl , palladium , methyl acrylate , heck reaction , ligand (biochemistry) , methanol , stereoselectivity , organic chemistry , base (topology) , ethyl acrylate , coupling reaction , catalysis , polymer chemistry , combinatorial chemistry , acrylate , copolymer , polymer , mathematical analysis , biochemistry , alkyl , receptor , mathematics
The Pd(OAc) 2 ‐catalyzed Heck reaction of aryl diazonium salts with 2‐arylacrylates led to cis ‐stilbenes with good to excellent stereoselectivity. The environmentally friendly protocol developed in this work features low palladium loading in technical‐grade methanol at room temperature under base‐, additive‐, and ligand‐free conditions. The same protocol applied to simple Heck coupling of aryl diazonium salts with methyl acrylate allows astonishingly low palladium loading, down to 0.005 mol %. The stereoselectivity experimentally observed for the synthesis of cis ‐stilbenes has been rationalized by DFT calculations. Moreover, the role of methanol in promoting the reaction has been clarified by a computational study.