Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 51, Pages 18571-18575Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201504165
Keywords
alkynes; gold; heterocycles; homogeneous catalysis; ring expansion
Categories
Funding
- National Natural Science Foundation of China [21125210, 21421091, 21372244, 21572256]
- Chinese Academy of Science
- Major State Basic Research Development Program [2011CB808700]
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A mild and efficient gold-catalyzed oxidative ring-expansion of a series of alkynyl heterocycles using pyridine-N-oxide as the oxidant has been developed, which affords highly valuable six- or seven-membered heterocycles with wide functional group toleration. The reaction consists of a regioselective oxidation and a chemoselective migration of an endocyclic carbon-heteroatom bond (favored over C-H migration) with the order of migratory aptitude for carbon-heteroatom bonds being C-S > C-N > C-O. In the absence of an oxidant, polycyclic products are readily constructed through a ring-expansion/Nazarov cyclization reaction sequence.
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