4.8 Article

Accessing alpha-Amino Ketyl Radicals from beta-Amino Alcohols via Chemoselective Hydrogen Atom Transfer Catalysis

Journal

ACS CATALYSIS
Volume 12, Issue 21, Pages 13186-13192

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.2c03724

Keywords

amino alcohols; radical reactions; ketyl radicals; hydrogen atom transfer; photocatalysis

Funding

  1. Fonds der Chemischen Industrie (Liebig fellowship)
  2. Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) [443074366]
  3. Bergische Universitaet Wuppertal
  4. MICINN of Spain [PID2021-126075NB-I00, IJC2020-045125-I]

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The study accomplished the effective extraction of alpha-hydroxy C-H bonds in beta-amino alcohols in complex molecules, leading to the synthesis of gamma-oxo-delta-amino esters, which are common in biologically active molecules.
The selective activation of a given C-H bond in complex molecules possessing bonds of similar polarity and strength remains one of the foremost challenges in hydrogen atom transfer (HAT) catalysis. Herein, we present the combination of photoredox and HAT catalysis with an oxophiic boron-based catalyst to achieve the chemoselective abstraction of alpha-hydroxy C-H bonds in beta-amino alcohols. This enables us to access alpha-amino ketyl radicals, which are exploited for the direct synthesis of gamma-oxo-delta-amino esters-a prominent scaffold in biologically active molecules.

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