Direct Synthesis of α-Aryl-α-Trifluoromethyl Alcohols via Nickel Catalyzed Cross-Electrophile Coupling

A nickel-catalyzed reductive cross-electrophile coupling between the redox-active N-trifluoroethoxyphthalimide and iodoarenes is documented. The protocol reproduces a formal arylation of trifluoroacetaldehyde under mild conditions in high yields (up to 88 %) and with large functional group tolerance (30 examples). A combined computational and experimental investigation revealed a pivotal solvent assisted 1,2-Hydrogen Atom Transfer (HAT) process to generate a nucleophilic alpha-hydroxy-alpha-trifluoromethyl C-centered radical for the Csp(2)-Csp(3) bond forming process.

Automated summary

This paper presents a nickel-catalyzed reductive cross-electrophile coupling reaction, which achieves high yields and high functional group tolerance in the arylation of trifluoroacetaldehyde through a solvent-assisted 1,2-Hydrogen Atom Transfer (HAT) process.