Journal
CHEMCATCHEM
Volume 7, Issue 23, Pages 3972-3977Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.201500724
Keywords
magnesium; manganese; palladium; phosphane ligands; reaction mechanisms
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Funding
- National Natural Sciences Foundation of China
- Specialized Research Fund for the Doctoral Program of Higher Education [20130031110013]
- MOE Innovation Team of China [IRT13022]
- Ministry of Education of China [B06005]
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An efficient direct carboxylation of a series of benzyl chlorides with CO2 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 MgCl2 as an indispensable additive. The reaction proceeded smoothly under 1 atm CO2. The application of Mn powder instead of a sensitive reducing reagent represents an operationally simple access to phenylacetic acids. Notably, MgCl2 is able to stabilize the (SPhos)(2)Pd-II(Bn)(Cl)(eta(1)-CO2)(MgCl2) adduct and thus facilitates CO2 insertion into the Pd-II-C bond, which is supported by a DFT study.
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