Synthesis of tetrahydrobenzo[b]furans via a gold(I)-catalyzed rearrangement/cycloisomerization sequence of cyclic 1-aryl-2-propargyl-cyclohex-2enols

Hsiao Feng Chen, Ming Chang P. Yeh

Research output: Contribution to journalArticle

Abstract

A facile synthesis of tetrahydrobenzo[b]furans via gold(I)-catalyzed cycloisomerization of 1-aryl-2-propargylcyclohex-2-enols is described. The transformation is suggested to proceed through a gold(I)-catalyzed tertiary allylic alcohol rearrangement to give a secondary allylic alcohol that underwent a 5-exo-dig addition of the hydroxyl group onto the gold(I)-activated alkyne to give a vinylgold species. Protodeauration of the resulting vinylgold intermediate followed by aromatization furnished the tetrahydrobenzo[b]furans.

Original languageEnglish
Pages (from-to)614-629
Number of pages16
JournalJournal of the Chinese Chemical Society
Volume66
Issue number6
DOIs
Publication statusPublished - 2019 Jun

Fingerprint

Furans
Gold
Aromatization
Alkynes
Hydroxyl Radical
allyl alcohol

Keywords

  • allylic alcohol
  • benzofuran
  • cycloisomerization
  • gold

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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abstract = "A facile synthesis of tetrahydrobenzo[b]furans via gold(I)-catalyzed cycloisomerization of 1-aryl-2-propargylcyclohex-2-enols is described. The transformation is suggested to proceed through a gold(I)-catalyzed tertiary allylic alcohol rearrangement to give a secondary allylic alcohol that underwent a 5-exo-dig addition of the hydroxyl group onto the gold(I)-activated alkyne to give a vinylgold species. Protodeauration of the resulting vinylgold intermediate followed by aromatization furnished the tetrahydrobenzo[b]furans.",
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author = "Chen, {Hsiao Feng} and Yeh, {Ming Chang P.}",
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T1 - Synthesis of tetrahydrobenzo[b]furans via a gold(I)-catalyzed rearrangement/cycloisomerization sequence of cyclic 1-aryl-2-propargyl-cyclohex-2enols

AU - Chen, Hsiao Feng

AU - Yeh, Ming Chang P.

PY - 2019/6

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N2 - A facile synthesis of tetrahydrobenzo[b]furans via gold(I)-catalyzed cycloisomerization of 1-aryl-2-propargylcyclohex-2-enols is described. The transformation is suggested to proceed through a gold(I)-catalyzed tertiary allylic alcohol rearrangement to give a secondary allylic alcohol that underwent a 5-exo-dig addition of the hydroxyl group onto the gold(I)-activated alkyne to give a vinylgold species. Protodeauration of the resulting vinylgold intermediate followed by aromatization furnished the tetrahydrobenzo[b]furans.

AB - A facile synthesis of tetrahydrobenzo[b]furans via gold(I)-catalyzed cycloisomerization of 1-aryl-2-propargylcyclohex-2-enols is described. The transformation is suggested to proceed through a gold(I)-catalyzed tertiary allylic alcohol rearrangement to give a secondary allylic alcohol that underwent a 5-exo-dig addition of the hydroxyl group onto the gold(I)-activated alkyne to give a vinylgold species. Protodeauration of the resulting vinylgold intermediate followed by aromatization furnished the tetrahydrobenzo[b]furans.

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