58-72-0Relevant academic research and scientific papers
Visible-light-induced photoredox-catalyzed synthesis of benzimidazo[2,1-a]iso-quinoline-6(5H)-ones
Wang, Bin,Zou, Long,Wang, Lei,Sun, Manman,Li, Pinhua
, p. 1229 - 1232 (2021)
A simple and efficient visible-light-induced photoredox-catalyzed diarylation of N-methacryloyl-2-arylbenzoimidazoles with aryl diazonium salts was developed. The reaction provides a convenient access to a variety of benzimidazoisoquinolinones through the construction of two C[sbnd]C bonds in one step under mild reaction conditions.
Pd-Catalyzed Coupling of N-Tosylhydrazones with Benzylic Phosphates: Toward the Synthesis of Di- or Tri-Substituted Alkenes
Zhang, Kena,Provot, Olivier,Alami, Mouad,Tran, Christine,Hamze, Abdallah
supporting information, p. 1249 - 1261 (2022/02/07)
This study shows that various di- and tri-substituted alkenes with high chemoselectivity were obtained in good to high yields by coupling N-tosylhydrazones (NTHs) with benzylic phosphates as electrophilic partners. The obtained new catalytic system consis
One-Pot Synthesis of Pentafluorophenyl Sulfonic Esters via Copper-Catalyzed Reaction of Aryl Diazonium Salts, DABSO, and Pentafluorophenol
Idris, Muhammad Aliyu,Lee, Sunwoo
supporting information, p. 4516 - 4520 (2021/05/26)
Pentafluorophenyl (PFP) sulfonic esters were synthesized via a copper-catalyzed one-pot multicomponent reaction of aryl diazonium tetrafluoroborate, DABSO (DABCO·(SO2)2), and pentafluorophenol. The reaction system provided the desired pentafluorophenyl sulfonic esters in good yields and exhibited excellent functional group tolerance. In addition, the generated PFP sulfonic esters were successfully applied in Sonogashira, Suzuki, Chan-Evans-Lam, and decarboxylative coupling reactions.
A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions
Huang, Binbin,Guo, Lin,Xia, Wujiong
supporting information, p. 2095 - 2103 (2021/03/26)
A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.
Method for hydrocarbylation synthesis of trisubstituted and tetrasubstituted olefins from non-terminal olefins
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Paragraph 0054-0068; 0085-0087, (2021/02/06)
The invention discloses a method for hydrocarbylation synthesis of trisubstituted and tetrasubstituted olefins from non-terminal olefins, wherein the method comprises the steps: carrying out hydrocarbylation reaction on the non-terminal olefins and sulfoxide in the presence of ferric salt and hydrogen peroxide, carrying out one-pot reaction on disubstituted non-terminal olefins to generate the trisubstituted olefins, and carrying out one-pot reaction on the trisubstituted non-terminal olefins to generate the tetrasubstituted olefins. In the method, sulfoxide is simultaneously used as a hydrocarbylation reagent and a solvent of olefins, and one more hydrocarbyl substituent is added to a reaction product compared with a double-bond carbon atom of a reactant, so that an olefin carbon chain isincreased; the reaction conditions are mild, the selectivity is good, the yield is high, and industrial production is facilitated.
Ni-catalyzed reductive decyanation of nitriles with ethanol as the reductant
Wu, Ke,Ling, Yichen,Sun, Nan,Hu, Baoxiang,Shen, Zhenlu,Jin, Liqun,Hu, Xinquan
supporting information, p. 2273 - 2276 (2021/03/09)
A nickel-catalyzed reductive decyanation of aromatic nitriles has been developed, in which the readily available and abundant ethanol was applied as the hydride donor. Various functional groups on the aromatic rings, such as alkoxyl, amino, imino and amide, were compatible in this catalytic protocol. Heteroaryl, benzylic and alkenyl nitriles were also tolerated. Mechanistic investigation indicated that ethanol provided hydride efficientlyviaβ-hydride elimination in this reductive decyanation.
Aryl acyl peroxides for visible-light induced decarboxylative arylation of quinoxalin-2(1: H)-ones under additive-, metal catalyst-, and external photosensitizer-free and ambient conditions
Xie, Long-Yong,Peng, Sha,Yang, Li-Hua,Peng, Cun,Lin, Ying-Wu,Yu, Xianyong,Cao, Zhong,Peng, Yu-Yu,He, Wei-Min
supporting information, p. 374 - 378 (2021/01/28)
Aryl radicals were generated for the first time from cheap and easily available aryl acyl peroxides in eco-friendly ethyl acetate under ambient conditions and visible-light illumination in the absence of any additive, metal catalyst, or external photosensitizer. The present arylation of quinoxalin-2(1H)-ones was chemo- and regioselective, and provided good access to various 3-arylquinoxalin-2(1H)-ones. This journal is
Direct C-H arylation of quinoxalinones with aryl acylperoxides under catalyst-free condition
Chen, Bajin,Wang, Shengpeng,Song, Jinxing,Wang, Xiaojun,Yu, Bencheng,Yang, Xiaobo
supporting information, (2020/12/07)
A simple and novel method for the direct C-H arylation of quinoxalinones with aryl acylperoxides has been developed. This reaction proceeded smoothly through a radical process under catalyst-free condition, giving the target products in moderate good yields. Such strategy provides a simple and green alternative for the synthesis of 3-arylquinoxalinones.
A donor-acceptor complex enables the synthesis of: E -olefins from alcohols, amines and carboxylic acids
Chen, Kun-Quan,Shen, Jie,Wang, Zhi-Xiang,Chen, Xiang-Yu
, p. 6684 - 6690 (2021/05/31)
Olefins are prevalent substrates and functionalities. The synthesis of olefins from readily available starting materials such as alcohols, amines and carboxylic acids is of great significance to address the sustainability concerns in organic synthesis. Metallaphotoredox-catalyzed defunctionalizations were reported to achieve such transformations under mild conditions. However, all these valuable strategies require a transition metal catalyst, a ligand or an expensive photocatalyst, with the challenges of controlling the region- and stereoselectivities remaining. Herein, we present a fundamentally distinct strategy enabled by electron donor-acceptor (EDA) complexes, for the selective synthesis of olefins from these simple and easily available starting materials. The conversions took place via photoactivation of the EDA complexes of the activated substrates with alkali salts, followed by hydrogen atom elimination from in situ generated alkyl radicals. This method is operationally simple and straightforward and free of photocatalysts and transition-metals, and shows high regio- and stereoselectivities.
Oxime ligands for Pd catalysis of the Mizoroki–Heck reaction, Suzuki–Miyaura coupling & annulation reactions
Bangar, Pronnoy G.,Nahide, Pradip D.,Meroliya, Heena K.,Waghmode, Shobha A.,Iyer, Suresh
, p. 308 - 316 (2020/10/06)
Monodentate and bidentate chelating oximes are readily available ligands for the Pd catalysis of the Mizoroki–Heck reaction and the Suzuki coupling. High yields were obtained in the Suzuki coupling in aqueous dioxane with TBABr as additive. The oximes can be easily synthesized from the corresponding ketones or aldehydes and thus provide a very large number of nitrogen-based ligands. They have the advantage of not undergoing oxidative degradation, common for phosphine ligands. Chelating oximes with Pd(OAc)2, activate aryl iodides to give high yields of the substitution products in the Mizoroki–Heck reactions as well as the Suzuki coupling. Acetophenone oxime ligand with Pd(OAc)2, catalyzed the reaction of aryl iodides with 1,2-disubstituted alkenes in moderate to high yields. As a test example, the LaRock indole annulation and synthesis of isocoumarin were achieved with acetophenone oxime ligand and Pd(OAc)2 in high yields.
