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Photo-induced Substitutive Introduction of the Aldoxime Functional Group to Carbon Chains: A Formal Formylation of Non-Acidic C(sp(3) )-H Bonds.

Authors
  • Kamijo, Shin1
  • Takao, Go2
  • Kamijo, Kaori2
  • Hirota, Masaki2
  • Tao, Keisuke2
  • Murafuji, Toshihiro3
  • 1 Graduate School of Science and Engineering and Graduate School of Sciences and Technology for Innovation, Yamaguchi University, Yamaguchi, 753-8512, Japan. [email protected] , (Japan)
  • 2 Graduate School of Science and Engineering and Graduate School of Sciences and Technology for Innovation, Yamaguchi University, Yamaguchi, 753-8512, Japan. , (Japan)
  • 3 Graduate School of Medicine, Yamaguchi University, Yamaguchi, 753-8512, Japan. , (Japan)
Type
Published Article
Journal
Angewandte Chemie International Edition in English
Publisher
Wiley (John Wiley & Sons)
Publication Date
Aug 08, 2016
Volume
55
Issue
33
Pages
9695–9699
Identifiers
DOI: 10.1002/anie.201603810
PMID: 27356038
Source
Medline
Keywords
Language
English
License
Unknown

Abstract

A photo-induced substitutive introduction of an aldoxime functional group to carbon chains was achieved using photo-excited 4-benzoylpyridine as a C(sp(3) )-H bond cleaving agent and arylsulfonyl oxime as an aldoxime precursor. The non-acidic C-H bonds in various substances, including cycloalkanes, ethers, azacycles, and cyclic sulfides, were chemoselectively converted at ambient temperature under neutral conditions. The present transformation is a formal formylation of non-acidic C(sp(3) )-H bonds in a single step. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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