113985-43-6Relevant articles and documents
Efficient Palladium-Catalyzed Coupling of Aryl Chlorides and Tosylates with Terminal Alkynes: Use of a Copper Cocatalyst Inhibits the Reaction
Gelman, Dmitri,Buchwald, Stephen L.
, p. 5993 - 5996 (2003)
Less catalyst, lower temperature, and greater generality are the advantages of the new general protocol over those previously described for the palladium-catalyzed coupling of aryl chlorides and alkynes (see scheme). Better results are obtained without a copper cocatalyst, which has been found to inhibit product formation in the coupling reaction of aryl chlorides with terminal alkynes.
Unusual regioselectivity in the aldehyde addition reactions of allenyl/propargyl zirconium complexes derived from γ-(2-Pyridyl)propargyl ethers: Synthesis of multisubstituted α-hydroxyallenes
Fan, Guoqin,Xie, Xin,Liu, Yuanhong,Li, Yuxue
supporting information, p. 1636 - 1642 (2013/05/08)
Zirconium-mediated reactions of γ-(2-pyridyl)propargyl ethers with aldehydes afford α-hydroxyallenes selectively via the formation of allenyl/propargyl zirconium species. The reaction outcome is quite different to that of the reactions using propargylic ethers without a pyridyl group reported so far, in which homopropargyl alcohols were formed predominantly. The structure of allenylzirconium intermediate has been confirmed by X-ray crystal analysis which reveals an intramolecular Zr-N coordination. DFT calculations suggest that the smaller steric effect of the pyridine ring compared with the phenyl ring and its capability to form hydrogen bondings with hydrogen atoms of the Cp ligand and the aldehyde may account for the observed regioselectivity.
Synthese regioselective par voie organometallique de pyridines, 4-picolines et 3,5-lutidines substituees en 2 par un groupe insature et/ou fonctionnel
Al-Arnaout, A.,Courtois, G.,Miginiac, L.
, p. 139 - 154 (2007/10/02)
A regioselective one-pot synthesis of 2-substituted pyridine derivatives from N-alkoxycarboxylpyridinium salts and α-unsaturated organozinc compounds is described.Similarly, functional alkynyl organomagnesium compounds lead to 2-alkynyl-ω-functional pyridines, from which (E)-2-alkenyl or 2-alkyl-ω-functional pyridines can be obtained by partial or complete reduction.
