期刊
ACS CATALYSIS
卷 11, 期 11, 页码 6510-6518出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.1c01108
关键词
gold catalysis; cyclization; 1,5-diyne; [5,5]-sigmatropic rearrangement; indeno[1,2-c]furans
资金
- CSC (China Scholarship Council)
- CONACyT (Mexico)
- Alexander von Humboldt Foundation
- Australian Research Council [DP180100904]
This study developed a highly efficient gold-catalyzed cycloisomerization reaction that tolerates various functional groups under mild conditions, providing a new approach for the synthesis of certain compounds. Through mechanistic studies, it was revealed that the product formation proceeds via a specific rearrangement reaction, which represents an unknown reactivity pattern in gold catalysis.
A highly efficient gold-catalyzed cycloisomerization of 1,5-diynes was developed. Various functional groups are tolerated under the mild reaction conditions, which provides an alternative approach for the synthesis of indeno[1,2-c]furans. On the basis of mechanistic studies, including crossover experiments, deuterium labeling, and computational chemistry, the product formation proceeds via a formal [5,5]-sigmatropic rearrangement, a yet unknown reactivity pattern in gold catalysis. Instead of a synchronous concerted [5,5]-sigmatropic rearrangement and beyond an asynchronous concerted mode, each involving a single transition state, two energetically low transition states (1.8 and 5.6 kJ/mol) and an intermediate associate of the migrating benzyl cation and the vinyl gold species could be located in the computations.
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