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Pati K, Gomes Gdos P, Harris T, et al. Fused Catechol Ethers from Gold(I)-Catalyzed Intramolecular Reaction of Propargyl Ethers with Acetals. Org Lett. 2016;18(5):928-31doi: 10.1021/acs.orglett.5b03522.
Pati, K., Gomes, G. d. o. s. . P., Harris, T., & Alabugin, I. V. (2016). Fused Catechol Ethers from Gold(I)-Catalyzed Intramolecular Reaction of Propargyl Ethers with Acetals. Organic letters, 18(5), 928-31. https://doi.org/10.1021/acs.orglett.5b03522
Pati, Kamalkishore, et al. "Fused Catechol Ethers from Gold(I)-Catalyzed Intramolecular Reaction of Propargyl Ethers with Acetals." Organic letters vol. 18,5 (2016): 928-31. doi: https://doi.org/10.1021/acs.orglett.5b03522
Pati K, Gomes Gdos P, Harris T, Alabugin IV. Fused Catechol Ethers from Gold(I)-Catalyzed Intramolecular Reaction of Propargyl Ethers with Acetals. Org Lett. 2016 Mar 04;18(5):928-31. doi: 10.1021/acs.orglett.5b03522. Epub 2016 Feb 17. PMID: 26886747.
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Org Lett. 2016 Mar 04;18(5):928-31. doi: 10.1021/acs.orglett.5b03522. Epub 2016 Feb 17.

Fused Catechol Ethers from Gold(I)-Catalyzed Intramolecular Reaction of Propargyl Ethers with Acetals.

Organic letters

Kamalkishore Pati, Gabriel dos Passos Gomes, Trevor Harris, Igor V Alabugin

Affiliations

  1. Department of Chemistry and Biochemistry, Florida State University , Tallahassee, Florida 32306, United States.

PMID: 26886747 DOI: 10.1021/acs.orglett.5b03522

Abstract

Selective gold(I)-catalyzed rearrangement of aromatic methoxypropynyl acetals leads to fused catechol ethers (1,2-dialkoxynapthalenes) in excellent yields. Furthermore, this process extends to the analogous heterocyclic and aliphatic substrates. Alkyne activation triggers nucleophilic addition of the acetal oxygen that leads to an equilibrating mixture of oxonium ions of similar stability. This mixture is "kinetically self-sorted" via a highly exothermic cyclization. Selective formation of 1,2-dialkoxy naphthalenes originates from chemoselective aromatization of the cyclic intermediate via 1,4-elimination of methanol.

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