α‐Benzylation of Carbonyl Compounds Enabled by Synergistic Copper/Amine Catalyzed Decarboxylation of Arylacetic Acids

Author:

Wen Kangmei1,Feng Mengxia2,Gao Qiwen1,Chen Chen1,Wu Yinrong1,Zhou Jiamin1,Huang Liangbin2ORCID,Tang Xiaodong1ORCID

Affiliation:

1. Guangdong Provincial Key Laboratory of New Drug Screening School of Pharmaceutical Sciences Southern Medical University 1838 Guangzhou Avenue North Guangzhou 510515 P. R. China

2. Key Laboratory of Functional Molecular Engineering of Guangdong Province School of Chemistry and Chemical Engineering South China University of Technology 381 Wushan Road Guangzhou 510640 P. R. China

Abstract

AbstractHerein, we report synergistic copper/amine‐catalyzed reactions for directly α‐benzylating carbonyl compounds with arylacetic acids. These reactions represent the first examples of decarboxylative oxidative synergistic transition‐metal/enamine catalysis for α‐functionalizing carbonyl compounds. The process features starting‐material availability, good functional group tolerance, mild reaction conditions, and good‐to‐excellent yields. Dibenzylated products were formed in moderate yields under slightly altered reaction conditions, and some products were transformed into 1,2,3,4‐tetrahydrocyclopenta[b]indole derivatives by acid‐catalyzed intermolecular cyclization reactions with indoles. Moreover, biological studies revealed that some products have anticancer properties and may be useful in drug‐discovery studies.magnified image

Funder

Basic and Applied Basic Research Foundation of Guangdong Province

Publisher

Wiley

Subject

General Chemistry

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