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

Author(s)

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

Affiliation

^[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

• Document type: Journal article
• Source: ADVANCED SYNTHESIS & CATALYSIS; v. 362, n. 12 APR 2020.
• Web of Science Citations: 0

Abstract

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)

• FAPESP's process: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
• Grantee: Arlene Gonçalves Corrêa
• Support Opportunities: Research Grants - Research Centers in Engineering Program
• FAPESP's process: 18/20956-5 - C-H Functionalization of Aliphatic and Aromatic Heterocycles by Visible Light Photoredox Catalysis
• Grantee: Marília Simão dos Santos
• Support Opportunities: Scholarships abroad - Research Internship - Post-doctor
• FAPESP's process: 17/03120-8 - Photochemical reactions applied to the synthesis of substituted indoles via radical insertion reactions to isonitriles
• Grantee: Marília Simão dos Santos
• Support Opportunities: Scholarships in Brazil - Post-Doctoral