A nickel-catalyzed reductive cross-electrophile coupling between the redox-active N-trifluoroeth-oxyphthalimide 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 theC sp2Csp3 bond forming process.

Lorenzo Lombardi, A.C. (2022). Direct Synthesis of α-Aryl-α-Trifluoromethyl Alcohols via Nickel Catalyzed Cross-Electrophile Coupling. ANGEWANDTE CHEMIE. INTERNATIONAL EDITION, 61(47), 1-6 [10.1002/anie.202211732].

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

Lorenzo Lombardi;Alessandro Cerveri;Riccardo Giovanelli;Giulio Bertuzzi
;
Marco Bandini
2022

Abstract

A nickel-catalyzed reductive cross-electrophile coupling between the redox-active N-trifluoroeth-oxyphthalimide 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 theC sp2Csp3 bond forming process.
2022
Lorenzo Lombardi, A.C. (2022). Direct Synthesis of α-Aryl-α-Trifluoromethyl Alcohols via Nickel Catalyzed Cross-Electrophile Coupling. ANGEWANDTE CHEMIE. INTERNATIONAL EDITION, 61(47), 1-6 [10.1002/anie.202211732].
Lorenzo Lombardi, Alessandro Cerveri, Riccardo Giovanelli, Marta Castiñeira Reis, Carlos Silva López, Giulio Bertuzzi, Marco Bandini...espandi
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/900643
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