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

Hai Huang; Luning Tang; Qi Liu; Yang Xi; Guangke He; Hongjun Zhu

doi:10.1039/c5cc10517j

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

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

School of Chemistry and Moleculai Engineering

Nanjing Tech University

Research output: Contribution to journal › Article › peer-review

19 Scopus citations

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.

Original language	English
Pages (from-to)	5605-5608
Number of pages	4
Journal	Chemical Communications
Volume	52
Issue number	32
DOIs	https://doi.org/10.1039/c5cc10517j
State	Published - 25 Apr 2016

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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.",

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AU - Huang, Hai

AU - Tang, Luning

AU - Liu, Qi

AU - Xi, Yang

AU - He, Guangke

AU - Zhu, Hongjun

PY - 2016/4/25

Y1 - 2016/4/25

N2 - 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.

AB - 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.

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

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