Transition metal-free C(sp3)–H bond coupling among three methyl groups

Yufeng Liu; Xi Zhan; Pengyi Ji; Jingwen Xu; Qiang Liu; Weiping Luo; Tieqiao Chen; Cancheng Guo

doi:10.1039/C7CC01309D

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Transition metal-free C(sp³)–H bond coupling among three methyl groups†

Yufeng Liu,

^a Xi Zhan,^a Pengyi Ji,^a Jingwen Xu,^a Qiang Liu,^a Weiping Luo,^a Tieqiao Chen^a and Cancheng Guo*^a

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* Corresponding authors

^a College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China
E-mail: ccguo@hnu.edu.cn
Fax: +86-731-88821488
Tel: +86-731-88821488

Abstract

A coupling of multiple C(sp³)–H bonds of the methyl group in methyl ketones with dimethyl sulfoxide is developed. This coupling allows the direct C(sp³)–H bond coupling among three methyl groups and affords one C–C bond and one C [double bond, length as m-dash] C bond under transition metal-free conditions. The value-added cyclized 3-methylthiomethyl chroman-4-ones can be synthesized through this method. A plausible mechanism is proposed.

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Article information

DOI: https://doi.org/10.1039/C7CC01309D
Article type: Communication
Submitted: 18 Feb 2017
Accepted: 18 Apr 2017
First published: 19 Apr 2017

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Chem. Commun., 2017,53, 5346-5349

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Transition metal-free C(sp³)–H bond coupling among three methyl groups

Y. Liu, X. Zhan, P. Ji, J. Xu, Q. Liu, W. Luo, T. Chen and C. Guo, Chem. Commun., 2017, 53, 5346 DOI: 10.1039/C7CC01309D

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Chemical Communications