Literature DB >> 20131915

Synthesis and reactivity of rhodium(II) N-triflyl azavinyl carbenes.

Neil Grimster1, Li Zhang, Valery V Fokin.   

Abstract

Highly reactive rhodium(II) N-trifluoromethylsulfonyl azavinyl carbenes are formed in situ from NH-1,2,3-triazoles, triflic anhydride, and rhodium carboxylates. They rapidly and selectively react with olefins, providing cyclopropane carboxaldehydes and 2,3-dihydropyrroles in generally excellent yields and high enantio- and diastereoselectivity.

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Year:  2010        PMID： 20131915      PMCID： PMC2834274          DOI： 10.1021/ja910187s

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


  9 in total

1.  Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion.

Authors:  Huw M L Davies; Rohan E J Beckwith
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

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

Authors:  Tony Horneff; Stepan Chuprakov; Natalia Chernyak; Vladimir Gevorgyan; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2008-10-15       Impact factor: 15.419

3.  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

Review 4.  Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion.

Authors:  Huw M L Davies; James R Manning
Journal:  Nature       Date:  2008-01-24       Impact factor: 49.962

5.  Efficient synthesis of 2-substituted-1,2,3-triazoles.

Authors:  Jarosław Kalisiak; K Barry Sharpless; Valery V Fokin
Journal:  Org Lett       Date:  2008-07-03       Impact factor: 6.005

6.  Rh-catalyzed intermolecular cyclopropanation with alpha-alkyl-alpha-diazoesters: catalyst-dependent chemo- and diastereoselectivity.

Authors:  Patricia Panne; Andrew DeAngelis; Joseph M Fox
Journal:  Org Lett       Date:  2008-06-12       Impact factor: 6.005

7.  Selectivity enhancement in the Rh(II)-catalyzed cyclopropanation of styrene with (silanyloxyvinyl)diazoacetates.

Authors:  Paul Müller; Gérald Bernardinelli; Yves F Allenbach; Maria Ferri; Howard D Flack
Journal:  Org Lett       Date:  2004-05-27       Impact factor: 6.005

8.  New syntheses of diazo compounds.

Authors:  Gerhard Maas
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  REGIOSELECTIVE SYNTHESIS OF EITHER 1H- OR 2H-1,2,3- TRIAZOLES VIA MICHAEL ADDITION TO α,ß-UNSATURATED KETONES.

Authors:  Sen Wai Kwok; Jason E Hein; Valery V Fokin; K Barry Sharpless
Journal:  Heterocycles       Date:  2008-11-01       Impact factor: 0.831
  9 in total
  25 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

2.  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

3.  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

4.  Rhodium-Catalyzed Intermolecular C-H Functionalization as a Key Step in the Synthesis of Complex Stereodefined β-Arylpyrrolidines.

Authors:  Robert W Kubiak; Huw M L Davies
Journal:  Org Lett       Date:  2018-06-21       Impact factor: 6.005

5.  Versatile reactivity of rhodium-iminocarbenes derived from N-sulfonyl triazoles.

Authors:  Anton V Gulevich; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2013-01-07       Impact factor: 15.336

6.  Catalytic asymmetric transannulation of NH-1,2,3-triazoles with olefins.

Authors:  Sen Wai Kwok; Li Zhang; Neil P Grimster; Valery V Fokin
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-24       Impact factor: 15.336

7.  Rhodium-catalyzed NH insertion of pyridyl carbenes derived from pyridotriazoles: a general and efficient approach to 2-picolylamines and imidazo[1,5-a]pyridines.

Authors:  Yi Shi; Anton V Gulevich; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2014-10-21       Impact factor: 15.336

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.  Arylation of rhodium(II) azavinyl carbenes with boronic acids.

Authors:  Nicklas Selander; Brady T Worrell; Stepan Chuprakov; Subash Velaparthi; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2012-08-28       Impact factor: 15.419
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