Radical α,β-Dehydrogenation of Saturated Amides via α-Oxidation with TEMPO under Transition Metal-Free Conditions

Article abstract of DOI:10.1021/acs.joc.9b00872

A transition metal-free radical process for the selective α,β-dehydrogenation of saturated amides under mild conditions is developed. Utilizing radical activation strategy, the challenging issue associated with the low α-acidity of amides is resolved. For the first time, α,β-unsaturated Weinreb amides and acrylamides could be efficiently prepared directly from corresponding saturated amides. Mechanistic studies confirm the radical nature of this transformation. Two gram scale α,β-dehydrogenation have also been performed to demonstrate the utility of this method.

Full text of DOI:10.1021/acs.joc.9b00872

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Note
Radical #,#-Dehydrogenation of Saturated Amides via #-
Oxidation with TEMPO under Transition Metal-Free Conditions
Mei-Mei Wang, Guo-Hui Sui, Xian-Chao Cui, Hui Wang, Jian-Ping Qu, and Yan-Biao Kang
J. Org. Chem., Just Accepted Manuscript • DOI: 10.1021/acs.joc.9b00872 • Publication Date (Web): 04 Jun 2019
Downloaded from http://pubs.acs.org on June 4, 2019
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Supporting Information
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Notes
ACKNOWLEDGMENT
ö
REFERENCES
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