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

Authors :
Lombardi, Lorenzo
Cerveri, Alessandro
Giovanelli, Riccardo
Castiñeira Reis, Marta
Silva López, Carlos
Bertuzzi, Giulio
Bandini, Marco
Source :
Angewandte Chemie. 11/21/2022, Vol. 134 Issue 47, p1-6. 6p.
Publication Year :
2022

Abstract

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]

Details

Language :
English
ISSN :
00448249
Volume :
134
Issue :
47
Database :
Academic Search Index
Journal :
Angewandte Chemie
Publication Type :
Academic Journal
Accession number :
160200485
Full Text :
https://doi.org/10.1002/ange.202211732