134542-02-2Relevant articles and documents
Cascade 8πElectrocyclization/Benzannulation to Access Highly Substituted Phenylpyridines
Du, Luan,Gong, Yiliang,Han, Jingpeng,Li, Baosheng,Li, You,Luo, Han,Tian, Yi,Xin, Xiaolan
supporting information, p. 7966 - 7971 (2021/10/25)
A cascade 8πelectrocyclization/benzannulation reaction was developed to obtain the synthetically important highly substituted phenyl-pyridines. This method shows great potential in the rapid and inexpensive application of the scalable and operationally simple production of accessible substrates. On the basis of the resulting phenyl-pyridine products, a new Ru catalyst and bidentate ligand were designed and prepared, further demonstrating its high practicability.
Photoinduced Palladium-Catalyzed Carbofunctionalization of Conjugated Dienes Proceeding via Radical-Polar Crossover Scenario: 1,2-Aminoalkylation and beyond
Gevorgyan, Vladimir,Kurandina, Daria,Shing Cheung, Kelvin Pak,Yata, Tetsuji
supporting information, p. 9932 - 9937 (2020/06/27)
A photoinduced palladium-catalyzed 1,2-carbofunctionalization of conjugated dienes has been developed. This mild modular approach, which does not require employment of exogeneous photosensitizers and external oxidants, allows for efficient and highly regio- and stereoselective synthesis of a broad range of allylic amines from readily available 1,3-dienes, alkyl iodides, and amines. Employment of O- and C-nucleophiles toward oxyalkylation and dialkylation products was also demonstrated. A putative π-allyl palladium radical-polar crossover path is proposed as a key event in this three-component coupling process. The utility of this protocol is highlighted by its application for derivatization of several amine-containing drugs.
A highly tunable stereoselective olefination of semistabilized triphenylphosphonium ylides with N -Sulfonyl imines
Dong, De-Jun,Li, Hai-Hua,Tian, Shi-Kai
supporting information; experimental part, p. 5018 - 5020 (2010/06/13)
The Wittig reaction involving direct olefination of triphenylphosphonium ylides (Ph3PCHR) with aldehydes is arguably the most often used method for alkene synthesis, but in general it yields mixtures of Z- and E-alkenes for semistabilized triphenylphosphonium ylides (R = aryl or vinyl). We have developed a simple and efficient protocol to improve the stereoselectivity significantly by replacing the aldehydes used in the Wittig reaction with N-sulfonyl imines, which possess distinct electronic and steric properties relative to aldehydes. A broad range of aromatic, α,β-unsaturated, and aliphatic imines bearing appropriate N-sulfonyl groups smoothly undergo olefination reaction with various benzylidenetriphenylphosphoranes or allylidenetriphenylphosphoranes under mild reaction conditions to afford an array of both Z- and E-isomers of conjugated alkenes in good to excellent yields and with greater than 99:1 stereoselectivity. Moreover, this tunable protocol has been successfully applied to the highly stereoselective synthesis of two anticancer agents, DMU-212 and its Z-isomer.
Mild and stereoconvergent palladium-catalyzed carbonyl alkenation reaction of α,β-unsaturated aldehydes
Braun, Manfred,Mross, Stefan,Schwarz, Ido
, p. 83 - 88 (2007/10/03)
The addition of preformed ketone and ester enolates to α,β-unsaturated aldehydes 1 followed by in situ protection leads to the carbonates 3, 7, 8, 11, and 13. They are converted into sensitive functionalized dienes 4, 9, 12, and 14 by a smooth palladium-c
Ethano- and Etheno-bridged 2-Pyridyl Isoxazoles and Thiazoles, and Their Reduced Variants
Campbell, M. M.,Cosford, N. D. P.,Rae, D. R.,Sainsbury, M.
, p. 765 - 770 (2007/10/02)
(E)-2-(2-Oxobut-3-enyl)pyridine 21, (E)-2-(but-1-en-3-ynyl)pyridine 7 and (E)-2-(buta-1,3-dienyl)pyridine 15 are precursors for 2-pyridyl etheno-bridged isoxazoles and thiazoles, and a range of specifically reduced variants.
