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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.,
Corrêa Arlene G.,
Paixão Márcio W.,
König Burkhard
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000167
Subject(s) - chemistry , alkyl , catalysis , halide , photochemistry , nickel , photocatalysis , radical , yield (engineering) , bromine , visible spectrum , photoredox catalysis , metal , coupling reaction , medicinal chemistry , inorganic chemistry , organic chemistry , materials science , physics , optoelectronics , metallurgy
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.