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

Autor(es)

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]

Afiliação do(s) autor(es)

^[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

• Tipo de documento: Artigo Científico
• Fonte: ORGANIC LETTERS; v. 22, n. 21, p. 8598-8602, NOV 6 2020.
• Citações Web of Science: 0

Resumo

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)

• Processo FAPESP: 13/07276-1 - CEPOF - Centro de Pesquisa em Óptica e Fotônica
• Beneficiário: Vanderlei Salvador Bagnato
• Modalidade de apoio: Auxílio à Pesquisa - Centros de Pesquisa, Inovação e Difusão - CEPIDs
• Processo FAPESP: 18/00106-7 - Reações Fotocatalisadas por Porfirinas em Condições de Fluxo Contínuo: Arilação de Sistemas Heterocíclicos e de Olefinas Ativadas
• Beneficiário: Kleber Thiago de Oliveira
• Modalidade de apoio: Auxílio à Pesquisa - Regular