Photoinduced Nitroarenes as Versatile Anaerobic Oxidants for Accessing Carbonyl and Imine Derivatives.

Autor: Mitchell JK; Department of Chemistry, New York University, New York, New York 10003, United States., Hussain WA; Department of Chemistry, New York University, New York, New York 10003, United States., Bansode AH; Department of Chemistry, New York University, New York, New York 10003, United States., O'Connor RM; Department of Chemistry, New York University, New York, New York 10003, United States., Wise DE; Department of Chemistry, New York University, New York, New York 10003, United States., Choe MH; Department of Chemistry, New York University, New York, New York 10003, United States., Parasram M; Department of Chemistry, New York University, New York, New York 10003, United States.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2023 Sep 08; Vol. 25 (35), pp. 6517-6521. Date of Electronic Publication: 2023 Aug 24.
DOI: 10.1021/acs.orglett.3c02292
Abstrakt: Herein, we report a protocol for the anaerobic oxidation of alcohols, amines, aldehydes, and imines promoted by photoexcited nitroarenes. Mechanistic studies support the idea that photoexcited nitroarenes undergo double hydrogen atom transfer (HAT) steps with alcohols and amines to provide the respective ketone and imine products. In the presence of aldehydes and imines, successive HAT and oxygen atom transfer (OAT) events occur to yield carboxylic acids and amides, respectively. This transformation is amenable to a continuous-photoflow setup, which led to reduced reaction times.
Databáze: MEDLINE