Issue 12, 2021
From the journal:

Organic Chemistry Frontiers

α-Trideuteration of methylarenes†

Lin Tie,a   Xiang-Huan Shan,a   Jian-Ping Qu ORCID logo *b  and  Yan-Biao Kang ORCID logo *a  

* Corresponding authors

a Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China
E-mail: ybkang@ustc.edu.cn

b Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China
E-mail: ias_jpqu@njtech.edu.cn

Abstract

An efficient and practical transition metal free α-trideuteration of methylarenes was developed. This process proceeds via an inexpensive base, such as sodium hydroxide or potassium tert-butoxide, prompted deprotonation and reprotonation of methylarenes in DMSO-d6 solvent. The reaction is applicable to a wide range of methylarenes and allows the introduction of a trideuteriomethyl group to aromatics with excellent selectivity.

Graphical abstract: α-Trideuteration of methylarenes

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Article information

DOI
https://doi.org/10.1039/D1QO00265A
Article type
Research Article
Submitted
15 Feb 2021
Accepted
01 Apr 2021
First published
08 Apr 2021

Org. Chem. Front., 2021,8, 2981-2984

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α-Trideuteration of methylarenes

L. Tie, X. Shan, J. Qu and Y. Kang, Org. Chem. Front., 2021, 8, 2981 DOI: 10.1039/D1QO00265A

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