Literature DB >> 26652926

Lewis Acid Mediated Vinylogous Additions of Enol Nucleophiles into an α,β-Unsaturated Platinum Carbene.

Paul A Allegretti1, Khoi Huynh1, Tarik J Ozumerzifon1, Eric M Ferreira1.   

Abstract

A variety of substituted indoles and benzofurans are accessed via a platinum catalyzed annulation and vinylogous addition of enol nucleophiles. Several β-dicarbonyl compounds participate in the reaction, as do α-nitro and α-cyano carbonyl species. Subjecting the indole products to acidic conditions results in the formation of fused heterocycles.

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Year:  2015        PMID： 26652926      PMCID： PMC4732870          DOI： 10.1021/acs.orglett.5b03246

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  40 in total

1.  Gold-catalyzed cycloisomerization reactions of 2-tosylaminophenylprop-1-yn-3-ols as a versatile approach for indole synthesis.

Authors:  Prasath Kothandaraman; Weidong Rao; Shi Jia Foo; Philip Wai Hong Chan
Journal:  Angew Chem Int Ed Engl       Date:  2010-06-21       Impact factor: 15.336

2.  Synthesis and functionalization of indoles through palladium-catalyzed reactions.

Authors:  Sandro Cacchi; Giancarlo Fabrizi
Journal:  Chem Rev       Date:  2005-07       Impact factor: 60.622

Review 3.  Practical methodologies for the synthesis of indoles.

Authors:  Guy R Humphrey; Jeffrey T Kuethe
Journal:  Chem Rev       Date:  2006-07       Impact factor: 60.622

4.  Reversal of the regiochemistry in the rhodium-catalyzed [4+3] cycloaddition between vinyldiazoacetates and dienes.

Authors:  Pablo E Guzmán; Yajing Lian; Huw M L Davies
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-29       Impact factor: 15.336

5.  Alkynoate synthesis through the vinylogous reactivity of rhodium(II) carbenoids.

Authors:  Damien Valette; Yajing Lian; John P Haydek; Kenneth I Hardcastle; Huw M L Davies
Journal:  Angew Chem Int Ed Engl       Date:  2012-07-16       Impact factor: 15.336

6.  Synthesis of indoles using visible light: photoredox catalysis for palladium-catalyzed C-H activation.

Authors:  Jochen Zoller; David C Fabry; Meria A Ronge; Magnus Rueping
Journal:  Angew Chem Int Ed Engl       Date:  2014-10-03       Impact factor: 15.336

Review 7.  Marine indole alkaloids: potential new drug leads for the control of depression and anxiety.

Authors:  Anna J Kochanowska-Karamyan; Mark T Hamann
Journal:  Chem Rev       Date:  2010-08-11       Impact factor: 60.622

8.  Total synthesis of N-methylwelwitindolinone D isonitrile.

Authors:  Vikram Bhat; Kevin M Allan; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2011-03-29       Impact factor: 15.419

9.  Synthesis of β-Heteroaryl Propionates via Trapping of Carbocations with π-Nucleophiles.

Authors:  Tsung-Hao Fu; Amy Bonaparte; Stephen F Martin
Journal:  Tetrahedron Lett       Date:  2009-07-01       Impact factor: 2.415

10.  Rh(III)-catalyzed tandem C-H allylation and oxidative cyclization of anilides: a new entry to indoles.

Authors:  Ana Cajaraville; Susana López; Jesús A Varela; Carlos Saá
Journal:  Org Lett       Date:  2013-08-22       Impact factor: 6.005
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  5 in total

1.  Platinum-Catalyzed α,β-Unsaturated Carbene Formation in the Formal Syntheses of Frondosin B and Liphagal.

Authors:  Khoi Q Huynh; Curtis A Seizert; Tarik J Ozumerzifon; Paul A Allegretti; Eric M Ferreira
Journal:  Org Lett       Date:  2016-12-20       Impact factor: 6.005

2.  C-C Bond Migration in the Cycloisomerization of 1,6-Enynes.

Authors:  Susan M Stevenson; Eric T Newcomb; Eric M Ferreira
Journal:  Org Chem Front       Date:  2016-06-30       Impact factor: 5.281

3.  Computational study of Ru-catalyzed cycloisomerization of 2-alkynylanilides.

Authors:  Xinghui Zhang; Shanshan Li; Xiaoli Wei; Yun Lei
Journal:  J Mol Model       Date:  2018-06-14       Impact factor: 1.810

4.  Regioselectivity Influences in Platinum-Catalyzed Intramolecular Alkyne O-H and N-H Additions.

Authors:  Jeff P Costello; Eric M Ferreira
Journal:  Org Lett       Date:  2019-12-09       Impact factor: 6.072

Review 5.  Last Decade of Unconventional Methodologies for the Synthesis of Substituted Benzofurans.

Authors:  Lucia Chiummiento; Rosarita D'Orsi; Maria Funicello; Paolo Lupattelli
Journal:  Molecules       Date:  2020-05-16       Impact factor: 4.411
  5 in total

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