Biomaterial Database

Nickel-catalysed denitrogenative alkyne insertion reactions of N-sulfonyl-1,2,3-triazoles. 2009

Tomoya Miura, and Motoshi Yamauchi, and Masahiro Murakami

Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan.

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.

UI	MeSH Term	Description	Entries
D009532	Nickel	A trace element with the atomic symbol Ni, atomic number 28, and atomic weight 58.69. It is a cofactor of the enzyme UREASE.
D009584	Nitrogen	An element with the atomic symbol N, atomic number 7, and atomic weight [14.00643; 14.00728]. Nitrogen exists as a diatomic gas and makes up about 78% of the earth's atmosphere by volume. It is a constituent of proteins and nucleic acids and found in all living cells.
D002384	Catalysis	The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction.	Catalyses
D003500	Cyclization	Changing an open-chain hydrocarbon to a closed ring. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Cyclizations
D013237	Stereoisomerism	The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D013450	Sulfones		Sulfone
D014230	Triazoles	Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.	Triazole
D015394	Molecular Structure	The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds.	Structure, Molecular,Molecular Structures,Structures, Molecular