2835-33-8Relevant academic research and scientific papers
Highly active and recyclable silica gel-supported palladium catalyst for mild cross-coupling reactions of unactivated heteroaryl chlorides
Lee, Dong-Hwan,Jung, Ji-Young,Jin, Myung-Jong
experimental part, p. 2024 - 2029 (2011/02/22)
Silica gel-supported β-ketoiminatophosphane-Pd complex (Pd@SiO 2) was shown to be a highly active and long-lived catalyst for aqueous Suzuki, Stille and Sonogashira coupling reactions of heteroaryl chlorides. A wide range of heteroaryl chlorides could be efficiently coupled with different nucleophilic partners in the presence of only 0.5 mol% catalyst and under mild conditions. This is one of the most powerful heterogeneous catalysts for the couplings of diverse heteroaryl chlorides. Furthermore, the catalyst could be reused with almost consistent activity. The Royal Society of Chemistry 2010.
Ring-closing metathesis reactions on azinium salts: Straightforward access to quinolizinium cations and their dihydro derivatives
Nunez, Ana,Abarca, Beatriz,Cuadro, Ana M.,Alvarez-Builla, Julio,Vaquero, Juan J.
scheme or table, p. 4166 - 4176 (2009/09/08)
(Chemical Equation Presented) The ring-closing metathesis reaction of 1-butenyl-2-vinylpyridinium salts and 2-butenyl-1-vinylpyridinium salts using Grubbs second generation and Hoveyda-Grubbs catalysts proved to be an efficient approach to 3,4-dihydro- and 1,2-dihydroquinolizinium salts and the corresponding quinolizinium derivatives by an improved thermal oxidation in the presence of Pd/C without solvent. A comparative study showed that the quinolizinium system was obtained in better yields through the 3,4-dihydroquinolizinium route, thus allowing the synthesis of quinolizinium derivatives or improvements in the yields of some examples reported previously.
Ligand coupling reactions of 2-pyridyl, 4-pyridyl and 2-pyrimidyl sulfoxides with grignard reagents
Oae, Shigeru,Takeda, Takeshi,Uenishi, Junichi,Wakabayashi, Shoji
, p. 179 - 182 (2007/10/03)
The ligand coupling reaction was extended to 3-and 4-pyridyl sulfoxides as well as the 2-pyrimidyl moiety with Grignard reagents. It was found that both 4-pyridyl and 2-pyrimidyl sulfoxides nicely underwent the ligand coupling reactions, but 3-pyridyl sulfoxide underwent ligand exchange.
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.
OCCURRENCE OF LIGAND COUPLING IN THE REACTIONS OF VARIOUS SULFOXIDES WITH GRIGNARD REAGENTS
Kawai, Tsutomu,Kodera, Yoichi,Furukawa, Naomichi,Oae, Shigeru,Ishida, Masahiro,et al.
, p. 139 - 148 (2007/10/02)
Ligand coupling reactions take place not only between benzyl and 2-pyridyl groups and two 2-pyridyl groups in the treatment of benzyl, alkyl and aryl 2-pyridyl sulfoxides with Grignard reagents, but also between such groups as p-benzenesulfonylphenyl, 4-pyridyl, 2-quinolyl and 2-pyrimidyl, and the benzyl group.There are cases in which ligand exchange precedes ligand coupling, especially with 2-heteroaryl groups.In addition, even some alkyl groups were found to couple with the 2-pyridyl group.The ease of coupling seems to be associated with the electronegativity of the coupling carbon atom of the ligand, when one compares the 13C NMR chemical shifts.
A Novel Regiospecific Synthesis of 2-Substituted Pyridines
Hanessian, Stephen,Kagotani, Masahiro
, p. 409 - 411 (2007/10/02)
A simple method is described for the mild and efficient conversion of pyridyl-2-alkylsulfonates into 2-alkyl and 2-arylpyridines.
LIGAND COUPLING THROUGH ?-SULFURANE --- COMPLETE RETENTION OF CONFIGURATION OF 1-PHENYLETHYL GROUP IN THE REACTION OF 1-PHENYLETHYL 2-PYRIDYL SULFOXIDE WITH GRIGNARD REAGENT
Oae, Shigeru,Kawai, Tsutomu,Furukawa, Naomichi
, p. 69 - 72 (2007/10/02)
The reaction of benzyl or 1-phenylethyl 2-pyridyl sulfoxide with Grignard reagent proceeds via a ?-sulfurane as an intermediate to give the coupling product, 2-benzylpyridine or 2-(1-phenylethyl)pyridine in quantitative yield.Stereochemistry for this reaction is complete retention at the benzylic carbon atom.
