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  • Selective Hydrogen Atom Abstraction through Induced Bond Polarization: Direct α-Arylation of Alcohols through Photoredox, HAT, and Nickel Catalysis.

Selective Hydrogen Atom Abstraction through Induced Bond Polarization: Direct α-Arylation of Alcohols through Photoredox, HAT, and Nickel Catalysis.

Angewandte Chemie (International ed. in English) (2018-03-01)
Jack Twilton, Melodie Christensen, Daniel A DiRocco, Rebecca T Ruck, Ian W Davies, David W C MacMillan
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Ir[FCF3(CF3)ppy]2(dtbbpy)PF6
Pricing and availability is not currently available.
Sigma-Aldrich
1,10-Phenanthroline nickel (ll) dibromide
Pricing and availability is not currently available.