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Synthesis 2013; 45(15): 2088-2092
DOI: 10.1055/s-0033-1338471
DOI: 10.1055/s-0033-1338471
special topic
Rhodium-Catalyzed Dimerization of Arylacetylenes and Addition of Malonates to 1,3-Enynes
Further Information
Publication History
Received: 22 February 2013
Accepted after revision: 02 April 2013
Publication Date:
08 May 2013 (online)
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Abstract
An 8-quinolinolato rhodium catalyst was found to be effective for head-to-tail selective dimerization of arylacetylenes. Formation of substituted cyclopentene and allene derivatives via alkyne dimerization and subsequent addition of malonates was also catalyzed by the 8-quinolinolato rhodium catalyst in the presence of cesium fluoride. One-pot reaction using palladium-catalyzed alkyne dimerization in conjunction with rhodium-catalyzed addition of malonates was also possible.
Key words
rhodium catalyst - aromatic terminal alkynes - head-to-tail dimerization - cyclopentene derivatives - allene derivativesSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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For reviews, see:
For examples of E-selective head-to-head dimerization, see:
For a recent example of a Z-selective head-to-head dimerization, see:
For a recent example of head-to-tail selective cross dimerization, see:
The difficulty in isolation of 3a has been commented: