Photoredox/Nickel Dual-Catalyzed Reductive Cross Coupling of Aryl Halides Using an Organic Reducing Agent
Author(s) -
Abhishek Dewanji,
Raoul F. Bülow,
Magnus Rueping
Publication year - 2020
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.0c00199
Subject(s) - chemistry , aryl , halide , catalysis , nickel , combinatorial chemistry , reducing agent , coupling (piping) , coupling reaction , dual (grammatical number) , organic chemistry , photochemistry , alkyl , mechanical engineering , art , literature , engineering
A successful protocol for the reductive aryl-aryl cross-coupling of polyfluorinated arenes with a broad range of aryl halides has been developed. Sequential carbon-fluorine bond cleavage and carbon-carbon bond formation are two of the important features of the reaction. Addition of an aryl radical anion to a nickel intermediate was achieved for the first time using polyfluoroarenes as radical precursors. This, in combination with the excellen para selectivity, paves the way for the synthesis of various new multifluorinated biaryl compounds.
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