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- Title
Selective Hydrogen Atom Abstraction through Induced Bond Polarization: Direct α‐Arylation of Alcohols through Photoredox, HAT, and Nickel Catalysis.
- Authors
Twilton, Jack; Christensen, Melodie; DiRocco, Daniel A.; Ruck, Rebecca T.; Davies, Ian W.; MacMillan, David W. C.
- Abstract
Abstract: The combination of nickel metallaphotoredox catalysis, hydrogen atom transfer catalysis, and a Lewis acid activation mode, has led to the development of an arylation method for the selective functionalization of alcohol α‐hydroxy C−H bonds. This approach employs zinc‐mediated alcohol deprotonation to activate α‐hydroxy C−H bonds while simultaneously suppressing C−O bond formation by inhibiting the formation of nickel alkoxide species. The use of Zn‐based Lewis acids also deactivates other hydridic bonds such as α‐amino and α‐oxy C−H bonds. This approach facilitates rapid access to benzylic alcohols, an important motif in drug discovery. A 3‐step synthesis of the drug Prozac exemplifies the utility of this new method.
- Subjects
HYDROGEN; ABSTRACTION reactions; ARYLATION; ALCOHOLS (Chemical class); NICKEL catalysts; OXIDATION-reduction reaction; LEWIS acids
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 19, p5467
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201800749