853-83-8Relevant academic research and scientific papers
Utilization of transition metal fluoride-based solid support catalysts for the synthesis of sulfonamides: Carbonic anhydrase inhibitory activity and: In silico study
Al-Rashida, Mariya,Ali, Deedar,Amjad, Sayyeda Tayyeba,Hameed, Abdul,Iftikhar, Shafia,Iqbal, Jamshed,Naseer, Muhammad Moazzam,Shafique, Zainab,Shah, Muhammad Raza,Sindhu, Tayyaba Allamgir
, p. 3165 - 3179 (2022/02/05)
The applications of solid support catalysts in catalyzing organic reactions are well-evident. In the present study, we explored a transition metal fluoride (FeF3) adsorbed on molecular sieves (4 ?) as a solid support catalyst for the preparation of sulfon
Pd(II)/(S)-t-BuPyOx-catalyzed asymmetric addition of arylboronic acids to N-sulfonyl-arylaldimines
Song, Kaixuan,Wen, Min,Shen, Kai,Fan, Chaogang,Yang, Zhenyu,Lin, Shaohui,Pan, Qinmin
supporting information, (2021/05/26)
The asymmetric version of Pd(II)/bipyridine-catalyzed nucleophilic addition of arylboronic acids to N-sulfonyl arylaldimines was developed, and excellent asymmetric induction was achieved by the use of chiral pyridinooxazoline ligand (S)-t-BuPyOx. Moistur
Development of a CuCl/phosphine system to catalyze phenylation and methylation of N-tosyl aldimines with phenylboronic andmethylboronic acids
Ashouri, Akram,Nasiri, Behzad,Pourian, Somayeh,Samadi, Saadi,Zamani, Hossein
, p. 575 - 581 (2021/01/13)
The addition of phenylboronic and methylboronic acids to activated aromatic aldimines was demonstrated in the presence of copper(I)-phosphine complexes. The desired products were obtained using copper chloride/phosphine, and potassium fluoride in under toluene reflux, in moderate-to-good yield and a suitable reaction time.
Site-Selective Electrochemical Benzylic C?H Amination
Hou, Zhong-Wei,Liu, Ding-Jin,Xiong, Peng,Lai, Xiao-Li,Song, Jinshuai,Xu, Hai-Chao
supporting information, p. 2943 - 2947 (2020/12/11)
C?H/N-H cross-coupling is an ideal strategy to synthesize various amines but remains challenging owing to the requirement for sacrificial chemical oxidants and the difficulty in controlling the regio- and chemo-selectivity. Herein we report a site-selective electrochemical amination reaction that can convert benzylic C?H bonds into C-N linkages via H2 evolution without need for external oxidants or metal catalysts. The synthetic strategy involves anodic cleavage of benzylic C?H to form a carbocation intermediate, which is then trapped with an amine nucleophile leading to C?N bond formation. Key to the success is to include HFIP as a co-solvent to modulate the oxidation potentials of the alkylbenzene substrate and the aminated product to avoid overoxidation of the latter.
Is the Electrophilicity of the Metal Nitrene the Sole Predictor of Metal-Mediated Nitrene Transfer to Olefins? Secondary Contributing Factors as Revealed by a Library of High-Spin Co(II) Reagents
Kalra, Anshika,Bagchi, Vivek,Paraskevopoulou, Patrina,Das, Purak,Ai, Lin,Sanakis, Yiannis,Raptopoulos, Grigorios,Mohapatra, Sudip,Choudhury, Amitava,Sun, Zhicheng,Cundari, Thomas R.,Stavropoulos, Pericles
, p. 1974 - 1996 (2021/06/28)
Recent research has highlighted the key role played by the electron affinity of the active metal-nitrene/imido oxidant as the driving force in nitrene additions to olefins to afford valuable aziridines. The present work showcases a library of Co(II) reage
Halogen-Bond-Induced Consecutive Csp3-H Aminations via Hydrogen Atom Transfer Relay Strategy
Alom, Nur-E,Ariyarathna, Jeewani P.,Bassiouni, Omar H.,Kaur, Navdeep,Kennell, Maureen L.,Li, Wei,Wu, Fan
, p. 2135 - 2140 (2020/04/09)
The utilization of a halogen bond in a number of chemical fields is well-known. Surprisingly, the incorporation of this useful noncovalent interaction in chemical reaction engineering is rare. We disclose here an uncommon use of halogen bonding to induce intermolecular Csp3-H amination while enabling a hydrogen atom transfer relay strategy to access privileged pyrrolidine structures directly from alkanes. Mechanistic studies support the presence of multiple halogen bond interactions at distinct reaction stages.
An efficient metal-free oxidative esterification and amination of benzyl C-H bond
Liu, Saiwen,Chen, Ru,He, Guowen,Zhang, Jin
, (2020/04/09)
An esterification and amination of benzylic C-H bonds was developed by using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) under metal- and iodide-free conditions. Both carboxylic acids and amines could be used as ideal coupling partners for the oxidati
Organocatalytic nitrenoid transfer: Metal-free selective intermolecular C(sp3)-H amination catalyzed by an iminium salt
Combee, Logan A.,Raya, Balaram,Wang, Daoyong,Hilinski, Michael K.
, p. 935 - 939 (2018/02/07)
This report details the first organocatalytic method for nitrenoid transfer and its application to intermolecular, site-selective C(sp3)-H amination. The method utilizes a trifluoromethyl iminium salt as the catalyst, iminoiodinanes as the nitrogen source, and substrate as the limiting reagent. Activated, benzylic, and aliphatic substrates can all be selectively functionalized in yields up to 87%. A mechanistic proposal for the observed reactivity supported by experimental evidence invokes the intermediacy of a diaziridinium salt or related organic nitrenoid, species that have not been previously explored for the purpose of C-H amination. Finally, examples of late-stage functionalization of complex molecules highlight the selectivity and potential utility of this catalytic method in synthesis.
Selective Deprotection of N -Tosyl Alkoxyamines Using Bistrifluoromethane Sulfonimide: Formation of Oxime Ethers
Azizi, Mohamed Salah,Cossy, Janine
supporting information, p. 2417 - 2421 (2018/11/23)
The detosylation of N -tosyl alkoxyamines was realized by treatment with benzaldehyde and bistrifluoromethane sulfonimide as the catalyst to afford the corresponding oxime ethers. The reaction is chemoselective as N -tosyl amines are not deprotected. A me
Reaction Route and Mechanism of the Direct N-Alkylation of Sulfonamides on Acidic Mesoporous Zeolite β-Catalyst
Fu, Wenqian,Shen, Runsheng,Bai, Enhui,Zhang, Lei,Chen, Qun,Fang, Zhongxue,Li, Guangchao,Yi, Xianfeng,Zheng, Anmin,Tang, Tiandi
, p. 9043 - 9055 (2018/09/11)
Development of highly active heterogeneous catalysts with strong acidity and mesoporous structure is a highly attractive strategy for organic synthesis. In this study, a mesoporous zeolite beta (HBeta-M) with bulky particle size and strong acidity was synthesized and used in the direct N-alkylation of sulfonamides with alcohols. The strongly acidic HBeta-M had a higher intrinsic activity with initial turnover frequency of 11 × 10-2 s-1 than those of H-form mordenite nanosheets (3.3 × 10-2 s-1) and montmorillonite (4.0 × 10-2 s-1) catalysts. The experiment and characterization results demonstrate that there are two parallel reaction routes on the acidic catalysts. One route is the reaction of benzhydrol with p-toluenesulfonamide (route I). Another route is the reaction of dibenzhydryl ether, arising from route I, with p-toluenesulfonamide (route II), which is found in this work. The reaction rate of route I (13 × 10-3 mol kg-1 s-1) was higher than that of route II (9.8 × 10-3 mol kg-1 s-1) on HBeta-M, but route II predominantly contributed to the formation of the target product with high selectivity. Hereby, a complete reaction mechanism is proposed in this work.
