Gold(I)-catalyzed regioselective inter-/intramolecular addition cascade of di- and triynes for direct construction of substituted naphthalenes

The Journal of Organic Chemistry
Saori NaoeHiroaki Ohno

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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Citations

Jun 9, 2016·The Journal of Organic Chemistry·Saori NaoeHiroaki Ohno
Feb 12, 2017·Journal of the American Chemical Society·Gabriel Dos Passos Gomes, Igor V Alabugin
Feb 19, 2014·Accounts of Chemical Research·A Stephen K Hashmi
Feb 28, 2015·Chemical Reviews·Liangbin HuangLukas J Gooßen
Jun 7, 2016·Chemical Society Reviews·Carlotta RaviolaMaurizio Fagnoni
Nov 20, 2014·Chemical Communications : Chem Comm·Leyre MarzoJosé Luis García Ruano
Jan 18, 2014·Organic & Biomolecular Chemistry·Mahalingam Sivaraman, Paramasivan T Perumal
Jul 8, 2016·Chemical Society Reviews·Abdullah M Asiri, A Stephen K Hashmi
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Feb 7, 2018·The Journal of Organic Chemistry·Anna G LyapunovaIrina A Balova
Nov 30, 2012·Organic Letters·Philip M ByersIgor V Alabugin
Nov 22, 2012·The Journal of Organic Chemistry·Sébastien BouvetChristine Greck
Jan 13, 2015·The Journal of Organic Chemistry·René LiedtkeGerhard Erker
Apr 21, 2018·Accounts of Chemical Research·Igor V Alabugin, Edgar Gonzalez-Rodriguez
Sep 10, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Luca C GreinerHiroaki Ohno

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