Direct Csp3–H methylenation of 2-arylacetamides using DMF/Me2NH-BH3 as the methylene source

Yuting Liu; Chang-Ling Wang; Hui-Min Xia; Zhijuan Wang; Yi-Feng Wang

doi:10.1039/C9OB00875F

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Direct Csp³–H methylenation of 2-arylacetamides using DMF/Me₂NH-BH₃ as the methylene source†

Yuting Liu,‡^a Chang-Ling Wang,‡^b Hui-Min Xia,^b Zhijuan Wang

*^a and Yi-Feng Wang

*^b

Author affiliations

* Corresponding authors

^a Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing, China
E-mail: ias_zjwang@njtech.edu.cn

^b Hefei National Laboratory for Physical Sciences at the Microscale, Center for Excellence in Molecular Synthesis of CAS, Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, China
E-mail: yfwangzj@ustc.edu.cn

Abstract

A direct Csp³–H methylenation of 2-arylacetamides using DMF/Me₂NH-BH₃ as the methylene source was developed. The formyl group of DMF delivered the carbon and one hydrogen atoms, and the Me₂NH-BH₃ donated the remaining one hydrogen atom. This protocol offers a new alternative to make useful 2-arylacrylamides from simple starting materials.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/C9OB00875F
Article type: Paper
Submitted: 18 Apr 2019
Accepted: 31 May 2019
First published: 31 May 2019

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Org. Biomol. Chem., 2019,17, 6153-6157

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Direct Csp³–H methylenation of 2-arylacetamides using DMF/Me₂NH-BH₃ as the methylene source

Y. Liu, C. Wang, H. Xia, Z. Wang and Y. Wang, Org. Biomol. Chem., 2019, 17, 6153 DOI: 10.1039/C9OB00875F

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Organic & Biomolecular Chemistry