Et2Zn‐Mediated Gem‐Dicarboxylation of Cyclopropanols with CO2

Author:

Liu Hongjian1,Shi Lei2,Tan Xiaobin1,Kang Bangxiong1,Luo Gen2,Jiang Huanfeng1,Qi Chaorong1ORCID

Affiliation:

1. Key Laboratory of Functional Molecular Engineering of Guangdong Province School of Chemistry and Chemical Engineering South China University of Technology Guangzhou 510640 China

2. Institutes of Physical Science and Information Technology Anhui University Hefei 230601 China

Abstract

AbstractAn unprecedented Et2Zn‐mediated gem‐dicarboxylation of C─C/C─H single bond of cyclopropanols with CO2 is disclosed, which provides a straightforward and efficient methodology for the synthesis of a variety of structurally diverse and useful malonic acids in moderate to excellent yields. The protocol features mild reaction conditions, excellent functional group compatibility, broad substrate scope, and facile derivatization of the products. DFT calculations confirm that the transition‐metal‐free transformation proceeds through a novel ring‐opening/α‐functionalization/ring‐closing/ring‐opening/β‐functionalization (ROFCOF) process, and 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) plays dual important roles in the transformation.

Funder

National Natural Science Foundation of China

Natural Science Foundation of Anhui Province

Key Technologies Research and Development Program

Publisher

Wiley

Subject

General Physics and Astronomy,General Engineering,Biochemistry, Genetics and Molecular Biology (miscellaneous),General Materials Science,General Chemical Engineering,Medicine (miscellaneous)

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