5957-85-7Relevant academic research and scientific papers
Cp*Rh(iii)/boron hybrid catalysis for directed C-H addition to β-substituted α,β-unsaturated carboxylic acids
Hirata, Yuki,Kojima, Masahiro,Matsunaga, Shigeki,Tanaka, Ryo,Yoshino, Tatsuhiko
supporting information, p. 76 - 79 (2021/12/29)
The C-H bond addition reaction of 2-phenylpyridine derivatives with α,β-unsaturated carboxylic acids catalyzed by Cp*Rh(iii)/BH3·SMe2is reported. Activation of C-H bonds with the rhodium catalyst and activation of α,β-unsaturated carboxylic acids with the boron catalyst cooperatively work, and a BINOL-urea hybrid ligand significantly improved the reactivity. With the optimized hybrid catalytic system, various β-disubstituted carboxylic acids were obtained under mild reaction conditions.
Chromium-Catalyzed Reductive Cleavage of Unactivated Aromatic and Benzylic C-O Bonds
Yuan, Shuqing,Ling, Liang,Tang, Jinghua,Luo, Meiming,Zeng, Xiaoming
, p. 3343 - 3350 (2021/07/02)
Reductive cleavage of aromatic and benzylic C-O bonds by chromium catalysis is reported. This deoxygenative reaction was promoted by low-cost CrCl 2precatalyst combined with poly(methyl hydrogen siloxane) as the mild reducing agent, providing a strategy in forming reduced motifs by cleavage of unactivated C-O bonds. A range of functional groups such as bromide, chloride, fluoride, hydroxyl, amino, and alkoxycarbonyl can be retained in the reduction.
Ruthenium-Catalyzed ortho- And meta-H/D Exchange of Arenes
Zhao, Liang-Liang,Liu, Wei,Zhang, Zengyu,Zhao, Hongyan,Wang, Qi,Yan, Xiaoyu
supporting information, p. 10023 - 10027 (2019/12/24)
Ruthenium-catalyzed aromatic H/D exchange in [D4]acetic acid has been developed. By using N-heteroarenes as directing groups, both ortho and meta positions are selectively deuterated with high levels of D incorporation. Moreover, this strategy provides an alternative way to achieve meta-C-H activation.
Ligand-promoted ruthenium-catalyzed: Meta C-H chlorination of arenes using N -chloro-2,10-camphorsultam
Fan, Zhoulong,Lu, Heng,Cheng, Zhen,Zhang, Ao
supporting information, p. 6008 - 6011 (2018/06/18)
A practical meta C-H chlorination protocol is established via a Ru(0)-catalyzed ortho-metalation strategy. The use of N-chloro-2,10-camphorsultam as a new chlorinating agent is crucial for the success of the current reaction and an N-heterocyclic carbene (NHC) ligand could significantly enhance the reactivity of the catalytic transformation. The mechanistic studies reveal that an unusual ortho C-H ruthenation relay process with ortho chlorination of the C-Ru bond is probably involved.
Facile C–H arylation using catalytically active terminal sulfurs of 2 dimensional molybdenum disulfide
Hwang, Eunhee,Mi Lee, Sae,Bak, Sora,Min Hwang, Hee,Kim, Hyunjung,Lee, Hyoyoung
supporting information, p. 3969 - 3973 (2018/10/02)
The first methodology of C–H arylation of heteroarene via 2D transition metal dichalcogenides that have catalytically active edge functional groups was described. The terminal sulfur groups could effectively catalyze a formation of an azo-linked intermediate with aryl diazonium salts, leading to produce heteroarenes with good yields. This novel methodology using bulk 2D transition metal dichalcogenides that have catalytically active edge functional groups can apply for various reactions to achieve C–C bond formation in the fields of heterogeneous catalysis that is easily separable, highly reusable, and inexpensive method.
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.
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.
Triarylbismuthanes as threefold aryl-transfer reagents in regioselective cross-coupling reactions with bromopyridines and quinolines
Rao, Maddali L.N.,Dhanorkar, Ritesh J.
supporting information, p. 5214 - 5228 (2014/10/15)
Cross-coupling studies using bromopyridines and bromoquinolines with triarylbismuths as threefold coupling reagents in substoichiometric amounts under Pd-catalysed conditions are disclosed. The reactivity was high with both mono- and dibromopyridyl substrates, and mono- and bis-couplings were carried out regioselectively. A library of monoaryl and diaryl pyridines was formed in high yields. A one-pot strategy provided a simple and straightforward synthesis of both symmetrical and unsymmetrical diarylpyridines. Arylations of 2-bromo- and 3-bromoquinolines were achieved with triarylbismuth reagents. This study demonstrates that triarylbismuths may be used as threefold arylating reagents for the synthesis of aryl pyridines and quinolines through couplings with bromopyridines and bromoquinolines under Pd-catalysed conditions. Copyright
