C(sp(3))-C(sp(3)) Cross-Coupling of Alkyl Bromides and Ethers Mediated by Metal and Visible Light Photoredox Catalysis

Autor(es)

Santos, Marilia S. ^{[1, 2]} ; Correa, Arlene G. ^[1] ; Paixao, Marcio W. ^[1] ; Koenig, Burkhard ^[2]

Afiliação do(s) autor(es)

^[1] Fed Univ Sao Carlos UFSCar, Dept Chem, Ctr Excellence Res Sustainable Chem CERSusChem, Rodovia Washington Luis, Km 235, BR-13565905 Sao Carlos, SP - Brazil

^[2] Univ Regensburg, Inst Organ Chem, Univ Str 31, D-93053 Regensburg - Germany

• Tipo de documento: Artigo Científico
• Fonte: ADVANCED SYNTHESIS & CATALYSIS; v. 362, n. 12 APR 2020.
• Citações Web of Science: 0

Resumo

We report a C(sp(3))-C(sp(3)) cross-coupling of alkyl bromides and alkyl chlorides with ethers by dual photoredox-nickel catalysis. The catalytic system comprises of the organic photocatalyst 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4-CzIPN) and bench stable nickel (II) acetylacetonate in the presence of visible-light, providing the coupling products in up to 92% yield. Preliminary mechanistic studies suggest two catalytic cycles, as well as the photogeneration of bromine or chlorine radicals from halide atoms that are present in the structures of the coupling partners. The halide radical mediates the hydrogen atom transfer event, avoiding the need of an additional HAT catalyst. (AU)

• Processo FAPESP: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
• Beneficiário: Arlene Gonçalves Corrêa
• Modalidade de apoio: Auxílio à Pesquisa - Programa Centros de Pesquisa em Engenharia
• Processo FAPESP: 18/20956-5 - Funcionalização C-H de heterociclos alifáticos e aromáticos via catálise fotoredox por luz visível
• Beneficiário: Marília Simão dos Santos
• Modalidade de apoio: Bolsas no Exterior - Estágio de Pesquisa - Pós-Doutorado
• Processo FAPESP: 17/03120-8 - Reações fotoquímicas aplicadas à síntese de indóis substituídos via reações de inserção de radicais a isonitrilas
• Beneficiário: Marília Simão dos Santos
• Modalidade de apoio: Bolsas no Brasil - Pós-Doutorado