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

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...

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Published inOrganic letters Vol. 24; no. 20; pp. 3652 - 3656
Main Authors Herron, Alastair N., Hsu, Ching-Pei, Yu, Jin-Quan
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 27.05.2022
Amer Chemical Soc
Subjects
Amines
Chemistry
Chemistry, Organic
Halogenation
Hydrogen
Nitrogen
Physical Sciences
Science & Technology
FUNCTIONALIZATION
C(SP)-H BONDS
AMINATION
ALKYLATION
GENERATION
FLUORINATION
PHOTOREDOX CATALYSIS
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Summary: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.
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Alastair N. Herron – Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, United States of America
Ching-Pei Hsu – Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, United States of America
All authors have given approval to the final version of the manuscript. A.N.H. designed the precursor, developed the reactions, explored the substrate scope and conducted mechanistic experiments. C.-P.H. prepared substrates, explored the substrate scope, and contributed ideas. J.-Q.Y. supervised the project.
Author Contributions
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01261