4423-81-8Relevant academic research and scientific papers
Transition-Metal-Free Decarboxylative Arylation of 2-Picolinic Acids with Arenes under Air Conditions
Zhang, Xitao,Feng, Xiujuan,Zhou, Chuancheng,Yu, Xiaoqiang,Yamamoto, Yoshinori,Bao, Ming
supporting information, p. 7095 - 7099 (2018/11/23)
A facile, transition-metal-free, and direct decarboxylative arylation of 2-picolinic acids with simple arenes is described. The oxidative decarboxylative arylation of 2-picolinic acids with arenes proceeds readily via N-chloro carbene intermediates to afford 2-arylpyridines in satisfactory to good yields under transition-metal-free conditions. This new type of decarboxylative arylation is operationally simple and scalable and exhibits high functional-group tolerance. Various synthetically useful functional groups, such as halogen atoms, methoxycarbonyl, and nitro, remain intact during the decarboxylative arylation of 2-picolinic acids.
Chelation-Assisted Copper-Mediated Direct Acetylamination of 2-Arylpyridine C-H Bonds with Cyanate Salts
Kianmehr, Ebrahim,Amiri Lomedasht, Yousef,Faghih, Nasser,Khan, Khalid Mohammed
, p. 6087 - 6092 (2016/07/23)
In this study, the coupling of 2-phenylpyridine derivatives and potassium cyanate through C-H bond functionalization in the presence of a copper salt is developed for the first time. By this protocol, various heteroarylated acetanilide derivatives are synthesized in good yields. 2-Phenylpyridines containing electron-donating and -withdrawing groups appear to be well-tolerated by this transformation.
Aryl/heteroaryl pentafluorobenzenesulfonates (ArOPFBs): New electrophilic coupling partners for room temperature Suzuki-Miyaura cross-coupling reactions
Joseph, Jayan T.,Sajith, Ayyiliath M.,Ningegowda, Revanna C.,Nagaraj, Archana,Rangappa,Shashikanth, Sheena
supporting information, p. 5106 - 5111 (2015/08/06)
The first cross-coupling reaction between aryl/heteroaryl pentafluorobenzenesulfonates and aryl/heteroaryl boronic acids under mild conditions is described. The successful synthesis of highly ortho substituted biaryls and high chemoselectivity of these bench stable intermediates over tosylates, triflates, mesylates, and chlorides increases its scope as a valuable cross-coupling partner. The generality of this protocol was further extended to other boron containing nucleophiles (boronates, trifluoroborates) and alkyl boronic acids.
Cobalt(III)-Catalyzed Directed C-H Coupling with Diazo Compounds: Straightforward Access towards Extended π-Systems
Zhao, Dongbing,Kim, Ju Hyun,Stegemann, Linda,Strassert, Cristian A.,Glorius, Frank
supporting information, p. 4508 - 4511 (2015/04/14)
The first highly efficient and scalable cobalt-catalyzed directed C-H functionalization with carbene precursors is presented. This methodology provides a modular route towards a new class of conjugated polycyclic hydrocarbons with tunable emission wavelengths both in solution and in the solid state.
RhIII-Catalyzed C-H Activation with Pyridotriazoles: Direct Access to Fluorophores for Metal-Ion Detection
Kim, Ju Hyun,Gensch, Tobias,Zhao, Dongbing,Stegemann, Linda,Strassert, Cristian A.,Glorius, Frank
supporting information, p. 10975 - 10979 (2015/09/15)
The first C-H bond activation with pyridotriazoles as coupling partners is presented using a RhIII catalyst. The pyridotriazoles can be used as new carbene precursors in C-H activation for direct access to novel fluorescent scaffolds. These tunable fluorophores can be applied for the detection of metal ions.
Copper-catalyzed aerobic synthesis of 2-arylpyridines from acetophenones and 1,3-diaminopropane
Xi, Long-Yi,Zhang, Ruo-Yi,Liang, Shuai,Chen, Shan-Yong,Yu, Xiao-Qi
supporting information, p. 5269 - 5271 (2015/01/09)
A copper-catalyzed reaction providing direct access to 2-arylpyridines from acetophenones and 1,3-diaminopropane is described. A range of electronically diverse acetophenones undergo this transformation, affording 2-arylpyridines in good yields. (Chemical Equation Presented).
Synthesis of solid 2-pyridylzinc reagents and their application in Negishi reactions
Colombe, James R.,Bernhardt, Sebastian,Stathakis, Christos,Buchwald, Stephen L.,Knochel, Paul
supporting information, p. 5754 - 5757 (2013/12/04)
In search of alternatives to unstable or unreliable 2-pyridylboron reagents, we have explored two new varieties of solid, moderately air-stable 2-pyridylzinc reagents. Both reagents can be manipulated in air and are competent nucleophiles in Negishi cross-coupling reactions.
