Copper porphyrin catalyzed esterification of C(sp3)–H via a cross-dehydrogenative coupling reaction

Hua-Hua Wang; Wei-Hong Wen; Huai-Bo Zou; Fan Cheng; Atif Ali; Lei Shi; Hai-Yang Liu; Chi-Kwong Chang

doi:10.1039/C6NJ03876J

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Copper porphyrin catalyzed esterification of C(sp³)–H via a cross-dehydrogenative coupling reaction†

Hua-Hua Wang,^a Wei-Hong Wen,^a Huai-Bo Zou,^b Fan Cheng,^a Atif Ali,^a Lei Shi,^c Hai-Yang Liu

*^a and Chi-Kwong Chang*^d

Author affiliations

* Corresponding authors

^a Department of Chemistry, Key Laboratory of Functional Molecular Engineering of Guangdong Province, South China University of Technology, Guangzhou 510641, China
E-mail: chhyliu@scut.edu.cn

^b Key Laboratory of Jiangxi University for Applied Chemistry & Chemical Biology, Yichun University, Yichun 336000, China

^c Department of Chemistry, Guangdong University of Education, Guangzhou 510303, China

^d Department of Chemistry, Michigan State University, E. Lansing, MI 48824, USA
E-mail: changc@msu.edu

Abstract

The crystal structure of 5,10,15,20-tetra(ethoxycarbonyl)porphyrin copper(II) showed that its central copper has a six-coordinate structure. An efficient copper porphyrin-catalyzed cross-dehydrogenative coupling (CDC) esterification reaction between C(sp³)–H and carboxylic acids using di-tert-butyl peroxide (DTBP) as an oxidant was established. The kinetic isotope effect (KIE) indicated that C(sp³)–H bond cleavage was the rate-determining step of this CDC reaction.

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Article information

DOI: https://doi.org/10.1039/C6NJ03876J
Article type: Paper
Submitted: 11 Dec 2016
Accepted: 28 Mar 2017
First published: 29 Mar 2017

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New J. Chem., 2017,41, 3508-3514

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Copper porphyrin catalyzed esterification of C(sp³)–H via a cross-dehydrogenative coupling reaction

H. Wang, W. Wen, H. Zou, F. Cheng, A. Ali, L. Shi, H. Liu and C. Chang, New J. Chem., 2017, 41, 3508 DOI: 10.1039/C6NJ03876J

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