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Electrochemical Benzylic C(sp³)-H Direct Amidation.

ABSTRACT: Amide bonds are ubiquitous and found in a myriad of functional molecules. Although formed in a reliable and robust fashion, alternative amide bond disconnections provide flexibility and synthetic control. Herein we describe an electrochemical method to form the non-amide C-N bond from direct benzylic C(sp³)-H amidation. Our approach is applied toward the synthesis of secondary amides by coupling secondary benzylic substrates with substituted primary benzamides. The reaction has been scaled up to a multigram scale in flow.

SUBMITTER: Choi A

PROVIDER: S-EPMC10825869 | biostudies-literature | 2024 Jan

REPOSITORIES: biostudies-literature

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Electrochemical Benzylic C(sp3)-H Direct Amidation.

Choi Anthony A Goodrich Oliver H OH Atkins Alexander P AP Edwards Matthew D MD Tiemessen David D George Michael W MW Lennox Alastair J J AJJ

Organic letters 20240116 3

Amide bonds are ubiquitous and found in a myriad of functional molecules. Although formed in a reliable and robust fashion, alternative amide bond disconnections provide flexibility and synthetic control. Herein we describe an electrochemical method to form the non-amide C-N bond from direct benzylic C(sp3)-H amidation. Our approach is applied toward the synthesis of secondary amides by coupling secondary benzylic substrates with substituted primary benzamides. The reaction has been s ...[more]

PMID: 38227550

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