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Molecules 2015, 20(6), 10131-10140; doi:10.3390/molecules200610131

An Alternative Method for Generating Arynes from ortho-Silylaryl Triflates: Activation by Cesium Carbonate in the Presence of a Crown Ether

Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan
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Academic Editors: Daesung Lee and Hiroto Yoshida
Received: 1 May 2015 / Accepted: 28 May 2015 / Published: 1 June 2015
(This article belongs to the Special Issue Development and Application of Aryne Chemistry in Organic Synthesis)
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Abstract

An alternative method for generating arynes from ortho-silylaryl triflates using cesium carbonate and 18-crown-6 is reported. The method was efficiently applied to a variety of reactions between several arynes and arynophiles. We also demonstrated that the efficiency of aryne generation is significantly affected by the alkali metal countercation of the carbonate. View Full-Text
Keywords: aryne; ortho-silylaryl triflate; cesium carbonate; crown ether aryne; ortho-silylaryl triflate; cesium carbonate; crown ether
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Yoshida, S.; Hazama, Y.; Sumida, Y.; Yano, T.; Hosoya, T. An Alternative Method for Generating Arynes from ortho-Silylaryl Triflates: Activation by Cesium Carbonate in the Presence of a Crown Ether. Molecules 2015, 20, 10131-10140.

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