Literature DB >> 21812453

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

Jeffrey C Culhane1, Valery V Fokin.   

Abstract

Sulfamoyl azides are readily generated from secondary amines and a novel sulfonyl azide transfer agent, 2,3-dimethyl-1H-imidazolium triflate. They react with alkynes in the presence of a CuTC catalyst forming 1-sulfamoyl-1,2,3-triazoles. The latter are shelf-stable progenitors of rhodium azavinyl carbenes, versatile reactive intermediates that, among other reactions, readily and asymmetrically add to olefins.

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Year:  2011        PMID： 21812453      PMCID： PMC3224852          DOI： 10.1021/ol201705k

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


  9 in total

1.  Sulfamoyl azides. Hydrolysis rates and hypotensive activity.

Authors:  W L Matier; W T Comer; D Deitchman
Journal:  J Med Chem       Date:  1972-05       Impact factor: 7.446

2.  Copper-catalyzed hydrative amide synthesis with terminal alkyne, sulfonyl azide, and water.

Authors:  Seung Hwan Cho; Eun Jeong Yoo; Imhyuck Bae; Sukbok Chang
Journal:  J Am Chem Soc       Date:  2005-11-23       Impact factor: 15.419

3.  Practical synthesis of amides from in situ generated copper(I) acetylides and sulfonyl azides.

Authors:  Michael P Cassidy; Jessica Raushel; Valery V Fokin
Journal:  Angew Chem Int Ed Engl       Date:  2006-05-05       Impact factor: 15.336

4.  Efficient synthesis of 1-sulfonyl-1,2,3-triazoles.

Authors:  Jessica Raushel; Valery V Fokin
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

5.  An efficient, inexpensive, and shelf-stable diazotransfer reagent: imidazole-1-sulfonyl azide hydrochloride.

Authors:  Ethan D Goddard-Borger; Robert V Stick
Journal:  Org Lett       Date:  2007-08-22       Impact factor: 6.005

6.  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

7.  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

8.  O- and N-sulfations of carbohydrates using sulfuryl imidazolium salts.

Authors:  Laura J Ingram; Ahmed Desoky; Ahmed M Ali; Scott D Taylor
Journal:  J Org Chem       Date:  2009-09-04       Impact factor: 4.354

9.  Efficient synthesis of sulfonyl azides from sulfonamides.

Authors:  Jessica Raushel; Suresh M Pitram; Valery V Fokin
Journal:  Org Lett       Date:  2008-07-17       Impact factor: 6.005
  9 in total
  7 in total

1.  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

2.  Chan-Lam coupling reaction of sulfamoyl azides with arylboronic acids for synthesis of unsymmetrical N-arylsulfamides.

Authors:  Suk-Young Won; Seo-Eun Kim; Yong-Ju Kwon; Inji Shin; Jungyeob Ham; Won-Suk Kim
Journal:  RSC Adv       Date:  2019-01-18       Impact factor: 4.036

3.  A Rh(II)-catalyzed multicomponent reaction by trapping an α-amino enol intermediate in a traditional two-component reaction pathway.

Authors:  Shunying Liu; Wenfeng Yao; Yuan Liu; Qinghua Wei; Jianghui Chen; Xiang Wu; Fei Xia; Wenhao Hu
Journal:  Sci Adv       Date:  2017-03-08       Impact factor: 14.136

4.  Targeted Diazotransfer Reagents Enable Selective Modification of Proteins with Azides.

Authors:  Jonas Lohse; Lotteke J Y M Swier; Ruben C Oudshoorn; Guillaume Médard; Bernhard Kuster; Dirk-Jan Slotboom; Martin D Witte
Journal:  Bioconjug Chem       Date:  2017-04-05       Impact factor: 4.774

5.  Light-induced metal-free transformations of unactivated pyridotriazoles.

Authors:  Ziyan Zhang; Dongari Yadagiri; Vladimir Gevorgyan
Journal:  Chem Sci       Date:  2019-07-25       Impact factor: 9.825

6.  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

7.  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
  7 in total

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