Merging photoredox with nickel catalysis: Coupling of α-carboxyl sp 3 -carbons with aryl halides
2014; American Association for the Advancement of Science; Volume: 345; Issue: 6195 Linguagem: Inglês
10.1126/science.1255525
ISSN1095-9203
AutoresZhiwei Zuo, Derek T. Ahneman, Lingling Chu, Jack A. Terrett, Abigail G. Doyle, David W. C. MacMillan,
Tópico(s)Catalytic C–H Functionalization Methods
ResumoOver the past 40 years, transition metal catalysis has enabled bond formation between aryl and olefinic (sp(2)) carbons in a selective and predictable manner with high functional group tolerance. Couplings involving alkyl (sp(3)) carbons have proven more challenging. Here, we demonstrate that the synergistic combination of photoredox catalysis and nickel catalysis provides an alternative cross-coupling paradigm, in which simple and readily available organic molecules can be systematically used as coupling partners. By using this photoredox-metal catalysis approach, we have achieved a direct decarboxylative sp(3)-sp(2) cross-coupling of amino acids, as well as α-O- or phenyl-substituted carboxylic acids, with aryl halides. Moreover, this mode of catalysis can be applied to direct cross-coupling of C(sp³)-H in dimethylaniline with aryl halides via C-H functionalization.
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