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Literature DB >> 20931987

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

Abstract

An efficient room-temperature method for the synthesis of 1-sulfonyl-1,2,3-triazoles from in situ generated copper(I) acetylides and sulfonyl azides is described. The copper(I) thiophene-2-carboxylate (CuTC) catalyst produces the title compounds under both nonbasic anhydrous and aqueous conditions in good yields.

Entities: Chemical Gene Species

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Year: 2010 PMID： 20931987 PMCID： PMC2982995 DOI： 10.1021/ol102087r

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

14 in total

1. Copper-catalyzed reaction cascade: direct conversion of alkynes into N-sulfonylazetidin-2-imines.

Authors: Matthew Whiting; Valery V Fokin
Journal: Angew Chem Int Ed Engl Date: 2006-05-05 Impact factor: 15.336

2. Copper-catalyzed synthesis of N-sulfonyl-1,2,3-triazoles: controlling selectivity.

Authors: Eun Jeong Yoo; Mårten Ahlquist; Seok Hwan Kim; Imhyuck Bae; Valery V Fokin; K Barry Sharpless; Sukbok Chang
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

Review 3. Copper-catalyzed azide-alkyne cycloaddition (CuAAC) and beyond: new reactivity of copper(I) acetylides.

Authors: Jason E Hein; Valery V Fokin
Journal: Chem Soc Rev Date: 2010-03-04 Impact factor: 54.564

4. Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides.

Authors: Christian W Tornøe; Caspar Christensen; Morten Meldal
Journal: J Org Chem Date: 2002-05-03 Impact factor: 4.354

5. 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

6. Polytriazoles as copper(I)-stabilizing ligands in catalysis.

Authors: Timothy R Chan; Robert Hilgraf; K Barry Sharpless; Valery V Fokin
Journal: Org Lett Date: 2004-08-19 Impact factor: 6.005

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. Nickel-catalysed denitrogenative alkyne insertion reactions of N-sulfonyl-1,2,3-triazoles.

Authors: Tomoya Miura; Motoshi Yamauchi; Masahiro Murakami
Journal: Chem Commun (Camb) Date: 2009-01-06 Impact factor: 6.222

9. Copper(I) complexes as catalysts for the synthesis of N-sulfonyl-1,2,3-triazoles from N-sulfonylazides and alkynes.

Authors: Israel Cano; M Carmen Nicasio; Pedro J Pérez
Journal: Org Biomol Chem Date: 2009-11-27 Impact factor: 3.876

Review 10. 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

21 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

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

1. Copper-catalyzed reaction cascade: direct conversion of alkynes into N-sulfonylazetidin-2-imines.

2. Copper-catalyzed synthesis of N-sulfonyl-1,2,3-triazoles: controlling selectivity.

Review 3. Copper-catalyzed azide-alkyne cycloaddition (CuAAC) and beyond: new reactivity of copper(I) acetylides.

4. Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides.

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

6. Polytriazoles as copper(I)-stabilizing ligands in catalysis.

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

8. Nickel-catalysed denitrogenative alkyne insertion reactions of N-sulfonyl-1,2,3-triazoles.

9. Copper(I) complexes as catalysts for the synthesis of N-sulfonyl-1,2,3-triazoles from N-sulfonylazides and alkynes.

Review 10. The growing applications of click chemistry.

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

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

3. Copper Mediated Coupling of 2-(Piperazine)-pyrimidine Iodides with Aryl Thiols using Cu(I)Thiophene-2-carboxylate.

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

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

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

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

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

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

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