Literature DB >> 21619004

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

Stepan Chuprakov1, Jamal A Malik, Mikhail Zibinsky, Valery V Fokin.   

Abstract

A highly efficient enantioselective C-H insertion of azavinyl carbenes into unactivated alkanes has been developed. These transition metal carbenes are directly generated from readily available and stable 1-sulfonyl-1,2,3-triazoles in the presence of chiral Rh(II) carboxylates and are used for C-H functionalization of alkanes to access a variety of β-chiral sulfonamides.

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Year:  2011        PMID： 21619004      PMCID： PMC3142877          DOI： 10.1021/ja202969z

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


  20 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.  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

3.  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

4.  trans-Directing ability of amide groups in cyclopropanation: application to the asymmetric cyclopropanation of alkenes with diazo reagents bearing two carboxy groups.

Authors:  David Marcoux; André B Charette
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

Review 5.  Small-molecule H-bond donors in asymmetric catalysis.

Authors:  Abigail G Doyle; Eric N Jacobsen
Journal:  Chem Rev       Date:  2007-12       Impact factor: 60.622

Review 6.  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

7.  Catalytic asymmetric cyclopropanation of heteroaryldiazoacetates.

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

8.  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

9.  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

Review 10.  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
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  27 in total

1.  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

2.  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

3.  Ring expansion and rearrangements of rhodium(II) azavinyl carbenes.

Authors:  Nicklas Selander; Brady T Worrell; Valery V Fokin
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-19       Impact factor: 15.336

4.  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

5.  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

6.  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

7.  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

8.  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

9.  Ruthenium-catalyzed cycloadditions of 1-haloalkynes with nitrile oxides and organic azides: synthesis of 4-haloisoxazoles and 5-halotriazoles.

Authors:  James S Oakdale; Rakesh K Sit; Valery V Fokin
Journal:  Chemistry       Date:  2014-07-24       Impact factor: 5.236

10.  Enantioselective Intermolecular C-H Functionalization of Allylic and Benzylic sp(3) C-H Bonds Using N-Sulfonyl-1,2,3-triazoles.

Authors:  Robert W Kubiak; Jeffrey D Mighion; Sidney M Wilkerson-Hill; Joshua S Alford; Tetsushi Yoshidomi; Huw M L Davies
Journal:  Org Lett       Date:  2016-06-22       Impact factor: 6.005
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