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Gold(I)-catalyzed regioselective inter-/intramolecular addition cascade of di- and triynes for direct construction of substituted naphthalenes.
J Org Chem. 2012 Jun 01; 77(11):4907-16.JO

Abstract

The gold-catalyzed cascade intermolecular addition-intramolecular carbocyclization reaction of dialkynylbenzenes was developed. In this reaction, regioselective addition of an external nucleophile toward the terminal alkyne and subsequent 6-endo-dig cyclization proceeded to give the 1,3-disubstituted naphthalenes in good yields. The direct synthesis of disubstituted chrysenes via a gold-catalyzed addition and double cyclization cascade using a triyne-type substrate was also achieved.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Naoe S
Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.
Suzuki Y
No affiliation info available
Hirano K
No affiliation info available
Inaba Y
No affiliation info available
Oishi S
No affiliation info available
Fujii N
No affiliation info available
Ohno H
No affiliation info available

MeSH

AlkynesCatalysisCyclizationGoldMolecular StructureNaphthalenesStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

22568806

Citation

Naoe, Saori, et al. "Gold(I)-catalyzed Regioselective Inter-/intramolecular Addition Cascade of Di- and Triynes for Direct Construction of Substituted Naphthalenes." The Journal of Organic Chemistry, vol. 77, no. 11, 2012, pp. 4907-16.
Naoe S, Suzuki Y, Hirano K, et al. Gold(I)-catalyzed regioselective inter-/intramolecular addition cascade of di- and triynes for direct construction of substituted naphthalenes. J Org Chem. 2012;77(11):4907-16.
Naoe, S., Suzuki, Y., Hirano, K., Inaba, Y., Oishi, S., Fujii, N., & Ohno, H. (2012). Gold(I)-catalyzed regioselective inter-/intramolecular addition cascade of di- and triynes for direct construction of substituted naphthalenes. The Journal of Organic Chemistry, 77(11), 4907-16. https://doi.org/10.1021/jo300771f
Naoe S, et al. Gold(I)-catalyzed Regioselective Inter-/intramolecular Addition Cascade of Di- and Triynes for Direct Construction of Substituted Naphthalenes. J Org Chem. 2012 Jun 1;77(11):4907-16. PubMed PMID: 22568806.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Gold(I)-catalyzed regioselective inter-/intramolecular addition cascade of di- and triynes for direct construction of substituted naphthalenes. AU - Naoe,Saori, AU - Suzuki,Yamato, AU - Hirano,Kimio, AU - Inaba,Yusuke, AU - Oishi,Shinya, AU - Fujii,Nobutaka, AU - Ohno,Hiroaki, Y1 - 2012/05/15/ PY - 2012/5/10/entrez PY - 2012/5/10/pubmed PY - 2012/9/14/medline SP - 4907 EP - 16 JF - The Journal of organic chemistry JO - J Org Chem VL - 77 IS - 11 N2 - The gold-catalyzed cascade intermolecular addition-intramolecular carbocyclization reaction of dialkynylbenzenes was developed. In this reaction, regioselective addition of an external nucleophile toward the terminal alkyne and subsequent 6-endo-dig cyclization proceeded to give the 1,3-disubstituted naphthalenes in good yields. The direct synthesis of disubstituted chrysenes via a gold-catalyzed addition and double cyclization cascade using a triyne-type substrate was also achieved. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/22568806/Gold_I__catalyzed_regioselective_inter_/intramolecular_addition_cascade_of_di__and_triynes_for_direct_construction_of_substituted_naphthalenes_ L2 - https://doi.org/10.1021/jo300771f DB - PRIME DP - Unbound Medicine ER -