69491-52-7Relevant academic research and scientific papers
Meta-Selective CAr-H Nitration of Arenes through a Ru3(CO)12-Catalyzed Ortho-Metalation Strategy
Fan, Zhoulong,Ni, Jiabin,Zhang, Ao
supporting information, p. 8470 - 8475 (2016/07/26)
The first example of transition metal-catalyzed meta-selective CAr-H nitration of arenes is described. With the use of Ru3(CO)12 as the catalyst and Cu(NO3)2·3H2O as the nitro source, a wide spectrum of arenes bearing diversified N-heterocycles or oximido as the directing groups were nitrated with meta-selectivity exclusively. Mechanism studies have demonstrated the formation of a new 18e-octahedral ruthenium species as a key ortho-CAr-H metalated intermediate, which may be responsible for the subsequent meta-selective electrophilic aromatic substitution (SEAr). Moreover, this approach provides a fast-track strategy for atom/step economical synthesis of many useful pharmaceutical molecules.
Scope of the inverse electron demand Diels-Alder reactions of 1,2,3-triazine
Anderson, Erin D.,Boger, Dale L.
supporting information; experimental part, p. 2492 - 2494 (2011/07/09)
Chemical equations presented. An examination of the scope of the inverse electron demand Diels-Alder reactions of the parent unsubstituted 1,2,3-triazine is described including the first report of its unique capabilities for participating in previously unexplored [4 + 2] cycloaddition reactions with heterodienophiles.
Inverse electron demand diels-alder reactions of 1,2,3-triazines: Pronounced substituent effects on reactivity and cycloaddition scope
Anderson, Erin D.,Boger, Dale L.
supporting information; experimental part, p. 12285 - 12292 (2011/09/16)
A systematic study of the inverse electron demand Diels-Alder reactions of 1,2,3-triazines is disclosed, including an examination of the impact of a C5 substituent. Such substituents were found to exhibit a remarkable impact on the cycloaddition reactivity of the 1,2,3-triazine without altering, and perhaps even enhancing, the intrinsic cycloaddition regioselectivity. The study revealed not only that the reactivity may be predictably modulated by a C5 substituent (R = CO2Me > Ph > H) but also that the impact is of a magnitude to convert 1,2,3-triazine (1) and its modest cycloaddition scope into a heterocyclic azadiene system with a reaction scope that portends extensive synthetic utility, expanding the range of participating dienophiles. Significantly, the studies define a now powerful additional heterocyclic azadiene, complementary to the isomeric 1,2,4-triazines and 1,3,5-triazines, capable of dependable participation in inverse electron demand Diels-Alder reactions, extending the number of complementary heterocyclic ring systems accessible with implementation of the methodology.
Palladium-catalyzed monoselective halogenation of C-H bonds: Efficient access to halogenated arylpyrimidines using calcium halides
Song, Bingrui,Zheng, Xiaojian,Mo, Jun,Xu, Bin
supporting information; experimental part, p. 329 - 335 (2010/04/28)
A wide variety of ortho-halogenated arylpyrimidines were prepared with high monoselectivity and functional-group tolerance by using calcium halides as crucial halogenating agents and cupric trifluoroacetate as oxidant in the presence of air.
Palladium-Catalyzed Regioselective C-H Bond ortho-Acetoxylation of Arylpyrimidines
Zheng, Xiaojian,Song, Bingrui,Xu, Bin
supporting information; experimental part, p. 4376 - 4380 (2010/10/04)
An efficient and regioselective palladium-catalyzed ortho C-H acetoxylation reaction was developed to afford, ortho monoacetoxylated arylpyrimidmes in good to excellent yields by using cupric trifluoroacetate as a cocatalyst. A wide variety of oxygenated
Copper(I)-promoted palladium-catalyzed cross-coupling of unsaturated tri-n-butylstannane with heteroaromatic thioether
Alphonse, France-Aimee,Suzenet, Franck,Keromnes, Anne,Lebret, Bruno,Guillaumet, Gerald
, p. 803 - 805 (2007/10/03)
(Matrix presented) Palladium-catalyzed cross-coupling of vinyl- and arylstannanes with π-electron-deficient heteroaromatics was performed in good yields. This Stille-type reaction was carried out with a methylthioether function as an electrophile in the presence of a copper(I) bromide-dimethyl sulfide complex.
