41880-26-6Relevant articles and documents
Selective Hydrogen Atom Abstraction through Induced Bond Polarization: Direct α-Arylation of Alcohols through Photoredox, HAT, and Nickel Catalysis
Twilton, Jack,Christensen, Melodie,DiRocco, Daniel A.,Ruck, Rebecca T.,Davies, Ian W.,MacMillan, David W. C.
, p. 5369 - 5373 (2018)
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.
