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Gold(I)-Catalyzed Intermolecular Aryloxyvinylation with Acetylene Gas.

ABSTRACT: Acetylene gas is an important feedstock for chemical production, although it is underutilized in organic synthesis. We have developed an intermolecular gold(I)-catalyzed alkyne/alkene reaction of o-allylphenols with acetylene gas that gives rise to chromanes by a stereospecific aryloxycyclization through the nucleophilic regioselective opening of cyclopropyl gold(I)-carbene intermediates. The synthetic application of this method was demonstrated in the late-stage functionalization of the natural product lapachol.

SUBMITTER: Medina-Gil T

PROVIDER: S-EPMC10442918 | biostudies-literature | 2023 Aug

REPOSITORIES: biostudies-literature

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Gold(I)-Catalyzed Intermolecular Aryloxyvinylation with Acetylene Gas.

Medina-Gil Tania T Sadurní Anna A Hammarback L Anders LA Echavarren Antonio M AM

ACS catalysis 20230801 16

Acetylene gas is an important feedstock for chemical production, although it is underutilized in organic synthesis. We have developed an intermolecular gold(I)-catalyzed alkyne/alkene reaction of <i>o</i>-allylphenols with acetylene gas that gives rise to chromanes by a stereospecific aryloxycyclization through the nucleophilic regioselective opening of cyclopropyl gold(I)-carbene intermediates. The synthetic application of this method was demonstrated in the late-stage functionalization of the ...[more]

PMID: 37614519

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