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Chemoselective ?,?-Dehydrogenation of Saturated Amides.

ABSTRACT: We report a method for the selective ?,?-dehydrogenation of amides in the presence of other carbonyl moieties under mild conditions. Our strategy relies on electrophilic activation coupled to in?situ selective selenium-mediated dehydrogenation. The ?,?-unsaturated products were obtained in moderate to excellent yields, and their synthetic versatility was demonstrated by a range of transformations. Mechanistic experiments suggest formation of an electrophilic SeIV species.

SUBMITTER: Teskey CJ 

PROVIDER: S-EPMC6348382 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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Chemoselective α,β-Dehydrogenation of Saturated Amides.

Teskey Christopher J CJ   Adler Pauline P   Gonçalves Carlos R CR   Maulide Nuno N  

Angewandte Chemie (International ed. in English) 20181207 2

We report a method for the selective α,β-dehydrogenation of amides in the presence of other carbonyl moieties under mild conditions. Our strategy relies on electrophilic activation coupled to in situ selective selenium-mediated dehydrogenation. The α,β-unsaturated products were obtained in moderate to excellent yields, and their synthetic versatility was demonstrated by a range of transformations. Mechanistic experiments suggest formation of an electrophilic Se<sup>IV</sup> species. ...[more]

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