Ene Reaction of Arynes with Alkynes

Thiruvellore Thatai Jayanth, Masilamani Jeganmohan, Mu-Jeng Cheng, San-Yan Chu, and Chien-Hong Cheng*
Department of Chemistry, Tsing Hua University, Hsinchu 30013, Taiwan
J. Am. Chem. Soc., 2006, 128 (7), pp 2232–2233
DOI: 10.1021/ja058418q
Publication Date (Web): January 28, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, chcheng@mx.nthu.edu.tw

Abstract

Abstract Image

Arynes, generated in situ from ortho-silylaryl triflates, undergo ene reaction with alkynes possessing propargylic hydrogen in the presence of KF/18-crown-6 in THF at room temperature to give substituted phenylallenes. Various terminal and internal alkynes as well as different arynes can be used to give the corresponding phenylallenes in good to moderate yields. The reaction of alkyne without propargylic hydrogen gave an acetylenic C−H addition product (a phenylalkyne) and a dehydro Diels−Alder product (a phenanthrene).

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History

  • Published In Issue February 22, 2006
  • Received December 12, 2005

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