1447730-07-5Relevant academic research and scientific papers
Enantioselective Synthesis of α-(Hetero)aryl Piperidines through Asymmetric Hydrogenation of Pyridinium Salts and Its Mechanistic Insights
Qu, Bo,Mangunuru, Hari P. R.,Tcyrulnikov, Sergei,Rivalti, Daniel,Zatolochnaya, Olga V.,Kurouski, Dmitry,Radomkit, Suttipol,Biswas, Soumik,Karyakarte, Shuklendu,Fandrick, Keith R.,Sieber, Joshua D.,Rodriguez, Sonia,Desrosiers, Jean-Nicolas,Haddad, Nizar,McKellop, Keith,Pennino, Scott,Lee, Heewon,Yee, Nathan K.,Song, Jinhua J.,Kozlowski, Marisa C.,Senanayake, Chris H.
supporting information, p. 1333 - 1337 (2018/03/09)
Enantioselective synthesis of α-aryl and α-heteroaryl piperidines is reported. The key step is an iridium-catalyzed asymmetric hydrogenation of substituted N-benzylpyridinium salts. High levels of enantioselectivity up to 99.3:0.7 er were obtained for a range of α-heteroaryl piperidines. DFT calculations support an outersphere dissociative mechanism for the pyridinium reduction. Notably, initial protonation of the final enamine intermediate determines the stereochemical outcome of the transformation rather than hydride reduction of the resultant iminium intermediate.
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.
Fluorine-containing aromatic derivatives of selective hydrogenation reduction method
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Paragraph 0215; 0216; 0217; 0218; 0254, (2017/11/27)
The invention discloses a selective hydrogenation reduction method of a fluorine-containing aromatic hydrocarbon derivative, and particularly discloses a preparation method of a compound shown in a general formula C1, C2 or C3. The preparation method comprises the following step of: reacting a compound shown in a general formula A1, A2 or A3 with a compound shown in a general formula B in the presence of a catalyst, thus forming the compound shown in the general formula C1, C2 or C3.
Palladium-catalyzed ortho-selective c-f activation of polyfluoroarenes with triethylsilane: A facile access to partially fluorinated aromatics
Chen, Zhao,He, Chun-Yang,Yin, Zengsheng,Chen, Liye,He, Yi,Zhang, Xingang
supporting information, p. 5813 - 5817 (2013/07/11)
PdF: A simple catalytic system, broad substrate scope, and high versatility provide a useful and facile access to partially fluorinated aromatics (see scheme). Tuning the reaction conditions enables a diverse range of product structures to be prepared. Copyright
Nickel-catalyzed ortho-selective hydrodefluorination of N-containing heterocycle-polyfluoroarenes
He, Yi,Chen, Zhao,He, Chun-Yang,Zhang, Xingang
, p. 873 - 877 (2013/08/23)
An effective and facile method for preparation of partially fluorinated aromatics via Nickel catalyzed, chelation-assisted ortho selective hydrodefluorination of polyfluoroarnes with triethylsilane has been developed, in which N-containing heterocycles were used as directing groups. The advantage of this protocol is its simple catalytic system with use of inexpensive and readily available NiCl2·6H2O as a catalyst. An effective and facile method for preparation of partially fluorinated aromatics via Nickel catalyzed, chelation-assisted ortho selective hydrodefluorination of polyfluoroarnes with triethylsilane has been developed, in which N-containing heterocycles were used as directing groups. Copyright
