Advanced search
Start date
Betweenand
Related content
(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Electron-Donor-Acceptor Complex-Enabled Flow Methodology for the Hydrotrifluoromethylation of Unsaturated beta-Keto Esters

Full text
Author(s):
Batista, Gabriel M. F. [1, 2] ; de Castro, Pedro P. [2] ; Dos Santos, Helio F. [2] ; de Oliveira, Kleber T. [1] ; Amarante, Giovanni W. [2]
Total Authors: 5
Affiliation:
[1] Univ Fed Sao Carlos, Dept Chem, BR-13565905 Sao Carlos, SP - Brazil
[2] Univ Fed Juiz de Fora, Dept Chem, BR-36036900 Juiz De Fora, MG - Brazil
Total Affiliations: 2
Document type: Journal article
Source: ORGANIC LETTERS; v. 22, n. 21, p. 8598-8602, NOV 6 2020.
Web of Science Citations: 0
Abstract

A novel electron-donor-acceptor (EDA) complex-enabled flow photochemical hydrotrifluoromethylation of unsaturated beta-keto esters is described. The developed protocol has an easy experimental procedure and does not require the use of transition-metal-based photocatalysts, allowing the isolation of 14 new compounds in up to 86% yield. Control experiments and computational studies revealed that the reaction proceeds through a Michael-type 1,4-addition of a trifluoromethyl radical, followed by a proton transfer step. Furthermore, the reaction could be scaled up to 1 mmol, and the final produce could be employed in the preparation of an isoxazolone and a pyrazolone as trifluoro-substituted heterocycles. (AU)

FAPESP's process: 13/07276-1 - CEPOF - Optics and Photonic Research Center
Grantee:Vanderlei Salvador Bagnato
Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC
FAPESP's process: 18/00106-7 - Photocatalyzed Reactions by using porphyrins and continuous flow conditions: Arylations of heterocycles and activated olefins.
Grantee:Kleber Thiago de Oliveira
Support Opportunities: Regular Research Grants