Issue 32, 2016
From the journal:

Chemical Communications

Formation of α-chalcogenyl acrylamides through unprecedented chalcogen-mediated metal-free oxyfunctionalization of ynamides with DMSO as an oxidant†

Hai Huang,a   Luning Tang,a   Qi Liu,a   Yang Xi,a   Guangke He*a  and  Hongjun Zhu*a  

* Corresponding authors

a Department of Applied Chemistry, College of Sciences, Nanjing Tech University, Nanjing 211816, People's Republic of China
E-mail: hegk@njtech.edu.cn, zhuhj@njtech.edu.cn

Abstract

A novel chalcogen-mediated oxyfunctionalization mode of ynamides for the synthesis of α-chalcogenyl acrylamides has been developed. Independent of metal catalysts, external oxidants and additives, this mild process afforded a range of structurally diverse α-chalcogenyl acrylamides, including α-selanyl acrylamides and α-tellanyl acrylamides. Interestingly, diverse ynamides tolerated in this approach gave different stereoselectivities.

Graphical abstract: Formation of α-chalcogenyl acrylamides through unprecedented chalcogen-mediated metal-free oxyfunctionalization of ynamides with DMSO as an oxidant

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Article information

DOI
https://doi.org/10.1039/C5CC10517J
Article type
Communication
Submitted
23 Dec 2015
Accepted
07 Mar 2016
First published
16 Mar 2016

Chem. Commun., 2016,52, 5605-5608

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Formation of α-chalcogenyl acrylamides through unprecedented chalcogen-mediated metal-free oxyfunctionalization of ynamides with DMSO as an oxidant

H. Huang, L. Tang, Q. Liu, Y. Xi, G. He and H. Zhu, Chem. Commun., 2016, 52, 5605 DOI: 10.1039/C5CC10517J

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