Room Temperature Coupling of Aryldiazoacetates with Boronic Acids Enhanced by Blue Light Irradiation

Autor(es)

da Silva, Amanda F. ^[1] ; Afonso, Marco A. S. ^[1] ; Cormanich, Rodrigo A. ^[1] ; Jurberg, Igor D. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Estadual Campinas, Dept Organ Chem, Inst Chem, Rua Monteiro Lobato 270, BR-13083862 Campinas, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: CHEMISTRY-A EUROPEAN JOURNAL; v. 26, n. 25 MAR 2020.
• Citações Web of Science: 0

Resumo

A visible-light-promoted photochemical protocol is reported for the coupling of aryldiazoacetates with boronic acids. This photochemical reaction shows great enhancement compared to the same protocol performed in the absence of light. Except for a few cases, the room temperature coupling in the dark (thermal process) generally does not work. When it does, it is likely to also involve free carbenes as key intermediates. Alternatively, photochemical reactions show a broad scope, can be performed under air and tolerate a wide variety of functional groups. Reaction-evolution monitoring, DFT calculations and control experiments have been used to evaluate the main aspects of this intricate mechanistic scenario. Biologically active molecules Adiphenine, Benactyzine and Aprophen have been prepared as examples of synthetic applications. (AU)

• Processo FAPESP: 18/03910-1 - Estudos físico-químicos de compostos orgânicos fluorados: abordagens experimental e teórica
• Beneficiário: Rodrigo Antonio Cormanich
• Modalidade de apoio: Auxílio à Pesquisa - Jovens Pesquisadores
• Processo FAPESP: 18/21979-9 - Estudos de físico-química orgânica em peróxidos e dissulfetos para entendimento de suas propriedades e reatividades
• Beneficiário: Marco Aurélio de Souza Afonso
• Modalidade de apoio: Bolsas no Brasil - Iniciação Científica
• Processo FAPESP: 17/24017-0 - Aplicação de Isoxazolonas em Síntese Orgânica
• Beneficiário: Igor Dias Jurberg
• Modalidade de apoio: Auxílio à Pesquisa - Regular