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. 2016 Aug 8;55(33):9695-9.
doi: 10.1002/anie.201603810. Epub 2016 Jun 29.

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

Shin Kamijo  1 , Go Takao  2 , Kaori Kamijo  2 , Masaki Hirota  2 , Keisuke Tao  2 , Toshihiro Murafuji  3
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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

Shin Kamijo et al. Angew Chem Int Ed Engl. .

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.

Keywords: 4-benzoylpyridine; C−H functionalization; aldoximes; photoreactions; radicals.

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