Journal
ACS CATALYSIS
Volume 9, Issue 2, Pages 1019-1025Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b04455
Keywords
gold; oxidation; cyclization; carbenes; diynes
Categories
Funding
- National Natural Science Foundation of China [21572186, 21622204, 21772161, 91545105]
- PCSIRT
- NFFTBS [J1310024]
- Science & Technology Cooperation Program of Xiamen [3502Z20183015]
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Carbene cascade reactions involving carbene/alkyne metathesis have attracted much attention over the past decades because this chemistry offers great potential to build complicated cyclic molecules. However, the formed vinyl metal carbenoids in these reactions are limited to exocyclic carbenes, and the generation of endocyclic vinyl carbene complexes remains unexplored. Here, we report an unprecedented gold-catalyzed oxidative cyclization of terminal diynes. Importantly, the generation of endocyclic vinyl carbene complexes was involved in this oxidative cyclization, which is distinctively different from previous protocols. This method allows the facile synthesis of various valuable naphthoquinones and carbazolequinones from readily available diynes under exceptionally mild reaction conditions and features a broad substrate scope and wide functional group tolerance. Moreover, theoretical calculations provide further evidence on the divergent selectivity of this cyclization reaction.
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