Literature DB >> 21848347

Reactivity of N-(1,2,4-triazolyl)-substituted 1,2,3-triazoles.

Mikhail Zibinsky1, Valery V Fokin.   

Abstract

Synthetically useful rhodium(II) carbenes were obtained from N-(1,2,4-triazolyl)-substituted 1,2,3-triazoles and Rh(II) carboxylates. The electron-withdrawing 1,2,4-triazolyl group reveals the heretofore unknown reactivity of nonsulfonyl 1,2,3-triazoles, which exhibit the reactivity of diazo compounds. The resulting carbenes provide ready asymmetric access to secondary homoaminocyclopropanes (80-95% ee, dr >20:1) via reactions with olefins and also engage in efficient transannulation reactions with nitriles.
© 2011 American Chemical Society

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Year:  2011        PMID： 21848347      PMCID： PMC3224851          DOI： 10.1021/ol201949h

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


  12 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

Review 2.  Catalytic carbene insertion into C-H bonds.

Authors:  Michael P Doyle; Richard Duffy; Maxim Ratnikov; Lei Zhou
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

Review 3.  Guiding principles for site selective and stereoselective intermolecular C-H functionalization by donor/acceptor rhodium carbenes.

Authors:  Huw M L Davies; Daniel Morton
Journal:  Chem Soc Rev       Date:  2011-03-01       Impact factor: 54.564

4.  Catalytic asymmetric cyclopropanation of heteroaryldiazoacetates.

Authors:  H M Davies; R J Townsend
Journal:  J Org Chem       Date:  2001-10-05       Impact factor: 4.354

5.  Expanding the scope of C-H amination through catalyst design.

Authors:  Christine G Espino; Kristin Williams Fiori; Mihyong Kim; J Du Bois
Journal:  J Am Chem Soc       Date:  2004-12-01       Impact factor: 15.419

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

Authors:  Neil Grimster; Li Zhang; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2010-03-03       Impact factor: 15.419

7.  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

8.  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 9.  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

10.  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
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  9 in total

1.  Rhodium(II)-catalyzed asymmetric sulfur(VI) reduction of diazo sulfonylamidines.

Authors:  Nicklas Selander; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2012-01-27       Impact factor: 15.419

2.  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

3.  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

4.  Rh(II)-mediated domino [4 + 1]-annulation of α-cyanothioacetamides using diazoesters: A new entry for the synthesis of multisubstituted thiophenes.

Authors:  Jury J Medvedev; Ilya V Efimov; Yuri M Shafran; Vitaliy V Suslonov; Vasiliy A Bakulev; Valerij A Nikolaev
Journal:  Beilstein J Org Chem       Date:  2017-11-30       Impact factor: 2.883

5.  Polycyclic Indoline-Benzodiazepines through Electrophilic Additions of α-Imino Carbenes to Tröger Bases.

Authors:  Alessandro Bosmani; Alejandro Guarnieri-Ibáñez; Sébastien Goudedranche; Céline Besnard; Jérôme Lacour
Journal:  Angew Chem Int Ed Engl       Date:  2018-05-14       Impact factor: 15.336

6.  Regiodivergent synthesis of pyrazino-indolines vs. triazocines via α-imino carbenes addition to imidazolidines.

Authors:  Alejandro Guarnieri-Ibáñez; Adiran de Aguirre; Céline Besnard; Amalia I Poblador-Bahamonde; Jérôme Lacour
Journal:  Chem Sci       Date:  2020-11-23       Impact factor: 9.825

7.  Diversity-oriented synthesis of heterocycles and macrocycles by controlled reactions of oxetanes with α-iminocarbenes.

Authors:  Alejandro Guarnieri-Ibáñez; Florian Medina; Céline Besnard; Sarah L Kidd; David R Spring; Jérôme Lacour
Journal:  Chem Sci       Date:  2017-06-12       Impact factor: 9.825

8.  Tandem 1,2-sulfur migration and (aza)-Diels-Alder reaction of β-thio-α-diazoimines: rhodium catalyzed synthesis of (fused)-polyhydropyridines, and cyclohexenes.

Authors:  Dongari Yadagiri; Pazhamalai Anbarasan
Journal:  Chem Sci       Date:  2015-07-10       Impact factor: 9.825

9.  Rhodium catalyzed diastereoselective synthesis of 2,2,3,3-tetrasubstituted indolines from N-sulfonyl-1,2,3-triazoles and ortho-vinylanilines.

Authors:  Dongari Yadagiri; Angula Chandra Shekar Reddy; Pazhamalai Anbarasan
Journal:  Chem Sci       Date:  2016-05-24       Impact factor: 9.825
  9 in total

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