Copper(II)-catalyzed C–H (sp3) oxidation and C–N cleavage: synthesis of methylene-bridged compounds using TMEDA as a carbon source in water

Dan Zhao; Yue Wang; Min-Xue Zhu; Qi Shen; Lei Zhang; Yun Du; Jian-Xin Li

doi:10.1039/C3RA40695D

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Copper(ii)-catalyzed C–H (sp³) oxidation and C–N cleavage: synthesis of methylene-bridged compounds using TMEDA as a carbon source in water†

Dan Zhao,^a Yue Wang,^a Min-Xue Zhu,^a Qi Shen,^a Lei Zhang,^a Yun Du^a and Jian-Xin Li*^a

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* Corresponding authors

^a State Key lab of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, P. R. China
E-mail: lijxnju@nju.edu.cn
Fax: +86-25-83686419
Tel: +86-25-83686419

Abstract

A green, simple, and efficient protocol for the selective methylenation via CuCl₂/oxygen-mediated C–H (sp³) oxidation and C–N cleavage using tetramethylethylenediamine (TMEDA) as a carbon source has been developed. The reactions were achieved in green solvent water under atmospheric conditions. The protocol exhibited a broad substrate scope including indoles, anilines, pyrroles and 1,3-dicarbonyls. Furthermore, two key intermediates of the reaction were successfully identified and the mechanism was explored.

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Article information

DOI: https://doi.org/10.1039/C3RA40695D
Article type: Paper
Submitted: 20 Oct 2012
Accepted: 08 Feb 2013
First published: 14 Feb 2013

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RSC Adv., 2013,3, 10272-10276

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Copper(II)-catalyzed C–H (sp³) oxidation and C–N cleavage: synthesis of methylene-bridged compounds using TMEDA as a carbon source in water

D. Zhao, Y. Wang, M. Zhu, Q. Shen, L. Zhang, Y. Du and J. Li, RSC Adv., 2013, 3, 10272 DOI: 10.1039/C3RA40695D

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