期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 55, 期 12, 页码 4040-4043出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201511438
关键词
acylation; C-H activation; cross-coupling; nickel; photochemistry
资金
- NIGMS [R01 GM100985]
- Bristol-Myers Squibb (BMS Center for Molecular Synthesis at Princeton)
- Eli Lilly
- Amgen
Using nickel and photoredox catalysis, the direct functionalization of C(sp(3))-H bonds of N-aryl amines by acyl electrophiles is described. The method affords a diverse range of -amino ketones at room temperature and is amenable to late-stage coupling of complex and biologically relevant groups. C(sp(3))-H activation occurs by photoredox-mediated oxidation to generate -amino radicals which are intercepted by nickel in catalytic C(sp(3))-C coupling. The merger of these two modes of catalysis leverages nickel's unique properties in alkyl cross-coupling while avoiding limitations commonly associated with transition-metal-mediated C(sp(3))-H activation, including requirements for chelating directing groups and high reaction temperatures.
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