Literature DB >> 18855475

Rhodium-catalyzed transannulation of 1,2,3-triazoles with nitriles.

Tony Horneff1, Stepan Chuprakov, Natalia Chernyak, Vladimir Gevorgyan, Valery V Fokin.   

Abstract

Stable and readily available 1-sulfonyl triazoles are converted to the corresponding imidazoles in good to excellent yields via a rhodium(II)-catalyzed reaction with nitriles. Rhodium iminocarbenoids are proposed intermediates.

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Year:  2008        PMID： 18855475      PMCID： PMC2668606          DOI： 10.1021/ja805079v

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  20 in total

1.  Recent Advances in Asymmetric Catalytic Metal Carbene Transformations.

Authors:  Michael P. Doyle; David C. Forbes
Journal:  Chem Rev       Date:  1998-04-02       Impact factor: 60.622

2.  A Convenient Method for the Preparation of (Z)-alpha,beta-Unsaturated Carbonyl Compounds.

Authors:  Douglass F. Taber; R. Jason Herr; Shawn K. Pack; John M. Geremia
Journal:  J Org Chem       Date:  1996-04-19       Impact factor: 4.354

3.  Regiodivergent metal-catalyzed rearrangement of 3-iminocyclopropenes into N-fused heterocycles.

Authors:  Stepan Chuprakov; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2007-09-25       Impact factor: 6.005

4.  Rh-catalyzed transannulation of pyridotriazoles with alkynes and nitriles.

Authors:  Stepan Chuprakov; Frank W Hwang; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  A study of the scope and regioselectivity of the ruthenium-catalyzed [3 + 2]-cycloaddition of azides with internal alkynes.

Authors:  Max M Majireck; Steven M Weinreb
Journal:  J Org Chem       Date:  2006-10-27       Impact factor: 4.354

6.  Rh-catalyzed intermolecular reactions of alkynes with alpha-diazoesters that possess beta-hydrogens: ligand-based control over divergent pathways.

Authors:  Patricia Panne; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2007-01-10       Impact factor: 15.419

7.  Ruthenium-catalyzed cycloaddition of alkynes and organic azides.

Authors:  Li Zhang; Xinguo Chen; Peng Xue; Herman H Y Sun; Ian D Williams; K Barry Sharpless; Valery V Fokin; Guochen Jia
Journal:  J Am Chem Soc       Date:  2005-11-23       Impact factor: 15.419

8.  Ruthenium-catalyzed azide-alkyne cycloaddition: scope and mechanism.

Authors:  Brant C Boren; Sridhar Narayan; Lars K Rasmussen; Li Zhang; Haitao Zhao; Zhenyang Lin; Guochen Jia; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2008-06-21       Impact factor: 15.419

Review 9.  The growing applications of click chemistry.

Authors:  John E Moses; Adam D Moorhouse
Journal:  Chem Soc Rev       Date:  2007-05-03       Impact factor: 54.564

10.  Mechanistic studies on the Cu-catalyzed three-component reactions of sulfonyl azides, 1-alkynes and amines, alcohols, or water: dichotomy via a common pathway.

Authors:  Eun Jeong Yoo; Mårten Ahlquist; Imhyuck Bae; K Barry Sharpless; Valery V Fokin; Sukbok Chang
Journal:  J Org Chem       Date:  2008-06-17       Impact factor: 4.354
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  45 in total

Review 1.  Transition-metal-catalyzed denitrogenative transannulation: converting triazoles into other heterocyclic systems.

Authors:  Buddhadeb Chattopadhyay; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2011-11-25       Impact factor: 15.336

Review 2.  Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature.

Authors:  C Oliver Kappe; Doris Dallinger
Journal:  Mol Divers       Date:  2009-04-21       Impact factor: 2.943

3.  Synthesis and reactivity of sulfamoyl azides and 1-sulfamoyl-1,2,3-triazoles.

Authors:  Jeffrey C Culhane; Valery V Fokin
Journal:  Org Lett       Date:  2011-08-03       Impact factor: 6.005

Review 4.  Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors:  Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2013-01-10       Impact factor: 60.622

5.  Catalytic asymmetric C-H insertions of rhodium(II) azavinyl carbenes.

Authors:  Stepan Chuprakov; Jamal A Malik; Mikhail Zibinsky; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2011-06-20       Impact factor: 15.419

6.  Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines.

Authors:  John M Bennett; Jonathan D Shapiro; Krystina N Choinski; Yingbin Mei; Sky M Aulita; Giovanny M Dominguez; Max M Majireck
Journal:  J Vis Exp       Date:  2018-01-03       Impact factor: 1.355

7.  Intramolecular transannulation of alkynyl triazoles via alkyne-carbene metathesis step: access to fused pyrroles.

Authors:  Yi Shi; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2013-10-04       Impact factor: 6.005

8.  Stereoselective 1,3-insertions of rhodium(II) azavinyl carbenes.

Authors:  Stepan Chuprakov; Brady T Worrell; Nicklas Selander; Rakesh K Sit; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2013-12-17       Impact factor: 15.419

9.  Transannulation of 1-sulfonyl-1,2,3-triazoles with heterocumulenes.

Authors:  Stepan Chuprakov; Sen Wai Kwok; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2013-03-15       Impact factor: 15.419

10.  Rhodium-catalyzed enantioselective cyclopropanation of olefins with N-sulfonyl 1,2,3-triazoles.

Authors:  Stepan Chuprakov; Sen Wai Kwok; Li Zhang; Lukas Lercher; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2009-12-23       Impact factor: 15.419
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