Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 27, Pages 7872-7876Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201502369
Keywords
decarboxylation; homogeneous catalysis; hypervalent compounds; photochemistry; ynonylation
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Funding
- National Basic Research Program of China [2014CB910304]
- National Natural Science Foundation of China [21272260, 21472230]
- Thousand Talents Program Young Investigator Award
- State Key Laboratory of Bioorganic and Natural Products Chemistry
- Chinese Academy of Sciences
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A combination of hypervalent iodine(III) reagents (HIR) and photoredox catalysis with visible light has enabled chemoselective decarboxylative ynonylation to construct ynones, ynamides, and ynoates. This ynonylation occurs effectively under mild reaction conditions at room temperature and on substrates with various sensitive and reactive functional groups. The reaction represents the first HIR/photoredox dual catalysis to form acyl radicals from -ketoacids, followed by an unprecedented acyl radical addition to HIR-bound alkynes. Its efficient construction of an mGlu5 receptor inhibitor under neutral aqueous conditions suggests future visible-light-induced biological applications.
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