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Palladium‐Catalyzed Carboxylation of Benzyl Chlorides with Atmospheric Carbon Dioxide in Combination with Manganese/Magnesium Chloride
Author(s) -
Zhang Shuai,
Chen WeiQiang,
Yu Ao,
He LiangNian
Publication year - 2015
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201500724
Subject(s) - carboxylation , chemistry , manganese , reagent , catalysis , magnesium , palladium , adduct , inorganic chemistry , chloride , phosphine , benzyl chloride , organic chemistry , medicinal chemistry
An efficient direct carboxylation of a series of benzyl chlorides with CO 2 catalyzed by Pd(OAc) 2 /dicyclohexyl (2′,6′‐dimethoxy‐[1,1′‐biphenyl]‐2‐yl)phosphine (SPhos) was developed to afford the corresponding phenylacetic acids in combination with Mn powder as a reducing reagent and MgCl 2 as an indispensable additive. The reaction proceeded smoothly under 1 atm CO 2 . The application of Mn powder instead of a sensitive reducing reagent represents an operationally simple access to phenylacetic acids. Notably, MgCl 2 is able to stabilize the (SPhos) 2 Pd II (Bn)(Cl)(η 1 ‐CO 2 )(MgCl 2 ) adduct and thus facilitates CO 2 insertion into the Pd II −C bond, which is supported by a DFT study.