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δ-C-H Halogenation Reactions Enabled by a Nitrogen-Centered Radical Precursor.

ABSTRACT: Nitrogen-centered radicals are versatile synthetic intermediates with the ability to undergo diverse reactions such as hydrogen atom transfer (HAT), β-scission, and addition across unsaturated systems. A long-standing impediment to the wider adoption of these intermediates in synthesis has been the difficulty of their generation. Herein we disclose a new hydrazonyl carboxylic acid precursor to nitrogen-centered radicals and its application toward remote C-H fluorination and chlorination reactions of sulfonyl-protected alkyl amines via 1,5-HAT.

SUBMITTER: Herron AN

PROVIDER: S-EPMC10292861 | biostudies-literature | 2022 May

REPOSITORIES: biostudies-literature

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δ-C-H Halogenation Reactions Enabled by a Nitrogen-Centered Radical Precursor.

Herron Alastair N AN Hsu Ching-Pei CP Yu Jin-Quan JQ

Organic letters 20220513 20

Nitrogen-centered radicals are versatile synthetic intermediates with the ability to undergo diverse reactions such as hydrogen atom transfer (HAT), β-scission, and addition across unsaturated systems. A long-standing impediment to the wider adoption of these intermediates in synthesis has been the difficulty of their generation. Herein we disclose a new hydrazonyl carboxylic acid precursor to nitrogen-centered radicals and its application toward remote C-H fluorination and chlorination reaction ...[more]

PMID: 35549294

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