Metallic reductant-free synthesis of α-substituted propionic acid derivatives through hydrocarboxylation of alkenes with a formate salt.
A PGeP-pincer palladium-catalyzed hydrocarboxylation of styrenes to obtain pharmaceutically important α-arylpropionic acid derivatives was achieved using a formate salt as both a reductant and a CO2source. The reaction was also applicable to vinylsulfone and acrylates. Isotope labeling experiments demonstrated that a CO2-recycling mechanism is operative through generation and reaction of a benzylpalladium complex as a carbon nucleophile. This protocol has realized a mild and atom economical CO2-fixation reaction without the necessity of using strong metallic reductants.
Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8551, Japan. niwasawa@chem.titech.ac.jp.
Jun
J
Takaya
Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8551, Japan. niwasawa@chem.titech.ac.jp.
Ko
K
Miyama
Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8551, Japan. niwasawa@chem.titech.ac.jp.
Chuan
C
Zhu
Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8551, Japan. niwasawa@chem.titech.ac.jp.
Nobuharu
http://orcid.org/0000-0001-6323-6588
N
Iwasawa