Facile synthesis of 1,2-aminoalcohols via α-C–H aminoalkylation of alcohols by photoinduced hydrogen-atom transfer catalysis

文献情報

出版日 2023-11-16

DOI 10.1039/D3SC05305A

インパクトファクター 9.825

著者

Joaquim Caner, Akira Matsumoto

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要旨

1,2-Aminoalcohols are common motifs found in a wide range of natural products and pharmaceutical compounds. Here we report a photocatalytic method for the direct conversion of readily available aliphatic alcohols into synthetically valuable 1,2-aminoalcohols. A dual catalytic system consisting of an acridinium photoredox catalyst and a cationic hydrogen-atom transfer (HAT) catalyst based on 1,4-diazabicyclo[2.2.2]octane (DABCO) enables an efficient and site-selective HAT from the α-C–H bonds of unprotected primary and secondary alcohols. The subsequent radical addition to a newly designed chiral N-sulfinyl α-iminoester afforded various 1,2-aminoalcohols, including enantiomerically enriched ones, under mild photochemical conditions with high atom and step economy.

掲載誌

Chemical Science

CiteScore: 14.4

自己引用率: 3.9%

年間論文数: 1413

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Facile synthesis of 1,2-aminoalcohols via α-C–H aminoalkylation of alcohols by photoinduced hydrogen-atom transfer catalysis

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