Journal
SCIENCE
Volume 345, Issue 6195, Pages 437-440Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.1255525
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Funding
- NIH [NIHGMS R01 GM103558-01, R01 GM100985-01]
- Shanghai Institute of Organic Chemistry
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Over 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 alpha-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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