Palladium‐Catalyzed Solvent‐Dependent Divergent Synthesis of Benzylformamides

A palladium‐catalyzed carbonylative cascade procedure for the synthesis of benzylformamides from aryl halides has been developed. The properties of the solvent chosen play a decisive role on the selectivity of the outcomes. Non‐coordinative solvent facilitates the coordination and insertion of CO to...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2018-09, Vol.360 (17), p.3412-3417
Main Authors: Wu, Fu‐Peng, Peng, Jin‐Bao, Qi, Xinxin, Ying, Jun, Wu, Xiao‐Feng
Format: Article
Language:English
Subjects:
Amines
Aromatic compounds
Aryl halides
Benzyl amine
Carbonylation
Carbonyls
Cascade reaction
Chemical synthesis
Cobalt
Functional groups
Halides
Palladium
Solvents
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Summary:A palladium‐catalyzed carbonylative cascade procedure for the synthesis of benzylformamides from aryl halides has been developed. The properties of the solvent chosen play a decisive role on the selectivity of the outcomes. Non‐coordinative solvent facilitates the coordination and insertion of CO to the amino‐palladium intermediate which then provides the formamides products. While the use of coordinative solvent leads to the formation of amines. A series of functional groups, including ester, ketone, nitro and cyano, were well tolerated under our conditions. The corresponding benzylformamides products were prepared in moderate to good yields without further optimization.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201800674