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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 α-hydroxy-α-trifluoromethyl C-centered radical for the Csp 2 -Csp 3 bond forming process., (© 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)

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 α‐hydroxy‐α‐trifluoromethyl C‐centered radical for the Csp2−Csp3 bond forming process. [ABSTRACT FROM AUTHOR]