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Synthesis 2016; 48(02): 223-230
DOI: 10.1055/s-0035-1560374
DOI: 10.1055/s-0035-1560374
paper
Silver-Promoted Oxidative Ring Opening/Alkynylation of Cyclopropanols: Facile Synthesis of 4-Yn-1-ones
Further Information
Publication History
Received: 19 September 2015
Accepted after revision: 16 October 2015
Publication Date:
17 November 2015 (online)
Abstract
A new silver-promoted oxidative ring opening/alkynylation of cyclopropanols with ethynylbenziodoxolones (EBX) is described. This method enables the formation of alkylated alkynes via a sequence of ring opening and alkynylation. Control experiments support a radical mechanism in this silver-promoted method.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560374.
- Supporting Information
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For selected reviews and papers:
During our prepare for this paper, a very similar report has come out. In this paper, excess amount of AcOH was required to promote the reaction with cyclopropanols. Furthermore, the scope is limited to silyl- and phenyl-substituted alkynes, see: