C(sp3)−C(sp3) Cross‐Coupling of Alkyl Bromides and Ethers Mediated by Metal and Visible Light Photoredox Catalysis. Issue 12 (28th April 2020)

• Record Type: Journal Article
• Authors: Santos, Marilia S.; Corrêa, Arlene G.; Paixão, Márcio W.; König, Burkhard
• Is Part Of: Advanced synthesis & catalysis. Volume 362:Issue 12(2020)
• Page Start: 2367
• Page End: 2372
• Publication Date: 2020-04-28
• Subjects: cross-coupling -- alkyl bromides -- dual catalysis -- visible-light -- nickel -- ethers; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202000167
• Languages: English
• ISSNs: 1615-4150

Abstract

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. Abstract :