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Synlett 2012; 23(12): 1725-1732
DOI: 10.1055/s-0031-1290401
DOI: 10.1055/s-0031-1290401
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Aryne Insertion Reactions into Carbon–Carbon σ-Bonds
Further Information
Publication History
Received: 29 February 2012
Accepted after revision: 24 April 2012
Publication Date:
21 June 2012 (online)
Abstract
Diverse nucleophilic carbon–electrophilic carbon σ-bonds were found to undergo facile cleavage and to add across carbon–carbon triple bonds of arynes without the aid of transition-metal catalysts, leading to the direct introduction of different carbon functionalities into the ortho-positions of aromatic rings. Active methylene compounds including β-dicarbonyl compounds, α-cyanocarbonyl compounds, sulfonylacetonitrile, and malononitrile smoothly underwent the aryne insertion reactions, and, moreover, the reaction was applicable to fluorene and trifluoromethyl ketone derivatives. The total synthesis of cytosporone B and phomopsin C, depending upon the carbon–carbon bond cleavage reaction, is also described.
1 Introduction
2 β-Dicarbonyl Compounds
3 α-Cyanocarbonyl Compounds
4 Sulfonylacetonitrile and Malononitrile
5 Fluorenes
6 Trifluoromethyl Ketones
7 Total Synthesis of Cytosporone B and Phomopsin C
8 Conclusion
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References
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For reviews, see:
For reviews, see:
Lithium (or sodium) enolates and α-lithionitriles underwent this type of reaction under strongly basic conditions using aryl halides as aryne precursors, see:
Stoltz and co-workers also reported natural product synthesis (amurensinine, curvularin and curvulin) utilizing the aryne insertion into carbon–carbon bonds, see: