Cu(II)-catalyzed C–H (SP3) oxidation and C–N cleavage: base-switched methylenation and formylation using tetramethylethylenediamine as a carbon source

Lei Zhang; Chen Peng; Dan Zhao; Yue Wang; Hai-Jian Fu; Qi Shen; Jian-Xin Li

doi:10.1039/C2CC32009F

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Cu(ii)-catalyzed C–H (SP³) oxidation and C–N cleavage: base-switched methylenation and formylation using tetramethylethylenediamine as a carbon source†

Lei Zhang,^a Chen Peng,^a Dan Zhao,^a Yue Wang,^a Hai-Jian Fu,^a Qi Shen^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

Base-switched methylenation and formylation using tetramethylethylenediamine (TMEDA) as a carbon source have been achieved under mild conditions, catalyzed by CuCl₂, with atmospheric oxygen as oxidant. Bisindolylmethanes, diphenylmethanes and 3-formylindoles were synthesized with excellent regioselectivity and good yield.

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Article information

DOI: https://doi.org/10.1039/C2CC32009F
Article type: Communication
Submitted: 19 Mar 2012
Accepted: 20 Apr 2012
First published: 23 Apr 2012

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Chem. Commun., 2012,48, 5928-5930

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Cu(II)-catalyzed C–H (SP³) oxidation and C–N cleavage: base-switched methylenation and formylation using tetramethylethylenediamine as a carbon source

L. Zhang, C. Peng, D. Zhao, Y. Wang, H. Fu, Q. Shen and J. Li, Chem. Commun., 2012, 48, 5928 DOI: 10.1039/C2CC32009F

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Chemical Communications