Deconstructive Carboxylation of Activated Alkenes with Carbon Dioxide

Author:

Yuan Pan‐Feng1,Yang Zhao12,Zhang Shan‐Shan12,Zhu Can‐Ming13,Yang Xiu‐Long2,Meng Qing‐Yuan13ORCID

Affiliation:

1. Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Molecular Recognition and Function Institute of Chemistry Chinese Academy of Sciences Beijing 100190 (P. R. China.

2. Key Laboratory of Chemical Biology of Hebei Province Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education and College of Chemistry and Environmental Science Hebei University Baoding 071002 P. R. China

3. University of Chinese Academy of Sciences Beijing 100049 P. R. China

Abstract

AbstractCarboxylation with carbon dioxide (CO2) represents one notable methodology to produce carboxylic acids. In contrast to carbon–heteroatom bonds, carbon–carbon bond cleavage for carboxylation with CO2 is far more challenging due to their inherent and less favorable orbital directionality for interacting with transition metals. Here we report a photocatalytic protocol for the deconstructive carboxylation of alkenes with CO2 to generate carboxylic acids in the absence of transition metals. It is emphasized that our protocol provides carboxylic acids with obviously unchanged carbon numbers when terminal alkenes were used. To show the power of this strategy, a variety of pharmaceutically relevant applications including the modular synthesis of propionate nonsteroidal anti‐inflammatory drugs and the late‐stage carboxylation of bioactive molecule derivatives are demonstrated.

Funder

National Natural Science Foundation of China

Publisher

Wiley

Subject

General Medicine

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