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Literature DB >> 19277359

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

Tomoya Miura¹, Motoshi Yamauchi, Masahiro Murakami.

Abstract

N-Sulfonyl-1,2,3-triazoles reacted with alkynes in the presence of a nickel(0)/phosphine catalyst to give substituted pyrroles, with the extrusion of molecular nitrogen; the triazole moiety isomerised to an alpha-imino diazo species, and the denitrogenative addition to nickel(0) was followed by the insertion of alkynes and reductive elimination.

Entities: Chemical

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Year: 2009 PMID： 19277359 DOI： 10.1039/b819162j

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

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Cited

18 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. A new reactivity mode for the diazo group: diastereoselective 1,3-aminoalkylation reaction of β-amino-α-diazoesters to give triazolines.

Authors: Alexey Kuznetsov; Anton V Gulevich; Donald J Wink; Vladimir Gevorgyan
Journal: Angew Chem Int Ed Engl Date: 2014-07-01 Impact factor: 15.336

Review 3. Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors: Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal: Chem Rev Date: 2013-01-10 Impact factor: 60.622

4. 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

5. 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

6. 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

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

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

2. A new reactivity mode for the diazo group: diastereoselective 1,3-aminoalkylation reaction of β-amino-α-diazoesters to give triazolines.

Review 3. Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

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

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

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

7. Rh-catalyzed transannulation of N-tosyl-1,2,3-triazoles with terminal alkynes.

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

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

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