Ene reaction of arynes with alkynes

Thiruvellore Thatai Jayanth; Masilamani Jeganmohan; Mu-Jeng Cheng; San Van Chu; Chien Hong Cheng

doi:10.1021/ja058418q

Ene reaction of arynes with alkynes

Thiruvellore Thatai Jayanth, Masilamani Jeganmohan, Mu-Jeng Cheng, San Van Chu, Chien Hong Cheng

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

60 Citations (Scopus)

Abstract

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).

Original language	English
Pages (from-to)	2232-2233
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	128
Issue number	7
DOIs	https://doi.org/10.1021/ja058418q
Publication status	Published - 2006 Feb 22

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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abstract = "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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AU - Jayanth, Thiruvellore Thatai

AU - Jeganmohan, Masilamani

AU - Cheng, Mu-Jeng

AU - Chu, San Van

AU - Cheng, Chien Hong

PY - 2006/2/22

Y1 - 2006/2/22

N2 - 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).

AB - 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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JO - Journal of the American Chemical Society

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Ene reaction of arynes with alkynes

Abstract

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