4.7 Article

Aniline-Type Hypervalent Iodine(III) for Intramolecular Cyclization via C-H Bond Abstraction of Hydrocarbons Containing N- and O-Nucleophiles

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 363, Issue 13, Pages 3354-3358

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202100316

Keywords

Aniline; C− H bond activation; Heterocycles; Hypervalent iodine; Intramolecular cyclization

Funding

  1. Ministry of Education, Culture, Sports, Science and Technology of Japan [G19K05469]

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A new synthetic method was developed with the use of aniline-type hypervalent iodine(III) for direct cyclizations, resulting in high yields of the corresponding products.
We developed a method for the preparation of (diacetoxyiodo)-2-(N-alkylamido)benzene as an aniline-type hypervalent iodine(III). We also achieved direct cyclizations via C-H bond abstraction, such as the Hofmann-Loffler-Freytag reaction, a direct amination, and a direct lactonization, using the aniline-type hypervalent iodine(III) to obtain corresponding products in high yields.

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