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Pd‐Catalyzed Synthesis of Vinyl Arenes from Aryl Halides and Acrylic Acid
Author(s) -
Gao Yang,
Ou Yang,
Gooßen Lukas J.
Publication year - 2019
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.201902022
Subject(s) - acrylic acid , halide , chemistry , catalysis , aryl , palladium , aryl halide , organic chemistry , cinnamic acid , combinatorial chemistry , polymer chemistry , polymer , alkyl , monomer
Acrylic acid is presented as an inexpensive, non‐volatile vinylating agent in a palladium‐catalyzed decarboxylative vinylation of aryl halides. The reaction proceeds through a Heck reaction of acrylic acid, immediately followed by protodecarboxylation of the cinnamic acid intermediate. The use of the carboxylate group as a deciduous directing group ensures high selectivity for monoarylated products. The vinylation process is generally applicable to diversely substituted substrates. Its utility is shown by the synthesis of drug‐like molecules and the gram‐scale preparation of key intermediates in drug synthesis.