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Synthesis 2021; 53(08): 1457-1470
DOI: 10.1055/s-0040-1706606
DOI: 10.1055/s-0040-1706606
paper
Gold Catalysis of Non-Conjugated Haloacetylenes
This work was supported by the Deutsche Forschungsgemeinschaft (DFG; HA 2973/17-1).
Abstract
Gold-catalyzed reactions of conjugated haloacetylenes are well known and usually result in the formation of addition or dimerization products. Herein, we report a gold-catalyzed reaction of non-conjugated haloacetylenes, which leads exclusively to the halogenated cyclization products. Remarkable is the gold-catalyzed reaction of tritylhaloacetylenes to haloindene derivatives, as mechanistic studies reveal that an 1,2-aryl shift occurs in the initially formed gold complex. The potential functionalization at the halogen atom and the wide scope of these cyclization reactions make them an attractive method for the construction of cyclic systems.
Key words
gold catalysis - haloacetylenes - indene - chromene - chromane - 1,2-aryl shift - cyclizationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706606.
- Supporting Information
Publication History
Received: 28 July 2020
Accepted after revision: 21 October 2020
Article published online:
26 November 2020
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