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Direct Synthesis of Enamides via Electrophilic Activation of Amides.

ABSTRACT: A novel, one-step N-dehydrogenation of amides to enamides is reported. This reaction employs the unlikely combination of LiHMDS and triflic anhydride, which serves as both the electrophilic activator and the oxidant, and is characterized by its simple setup and broad substrate scope. The synthetic utility of the formed enamides was readily demonstrated in a range of downstream transformations.

SUBMITTER: Spieß P

PROVIDER: S-EPMC8299460 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature

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Direct Synthesis of Enamides via Electrophilic Activation of Amides.

Spieß Philipp P Berger Martin M Kaiser Daniel D Maulide Nuno N

Journal of the American Chemical Society 20210707 28

A novel, one-step N-dehydrogenation of amides to enamides is reported. This reaction employs the unlikely combination of LiHMDS and triflic anhydride, which serves as both the electrophilic activator and the oxidant, and is characterized by its simple setup and broad substrate scope. The synthetic utility of the formed enamides was readily demonstrated in a range of downstream transformations. ...[more]

PMID: 34232035

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