7111-68-4Relevant academic research and scientific papers
Electrochemical Decarboxylative Cyclization of α-Amino-Oxy Acids to Access Phenanthridine Derivatives
Zhan, Yanling,Dai, Changhui,Zhu, Zitong,Liu, Ping,Sun, Peipei
supporting information, (2022/02/07)
Phenanthridines are a class of useful heterocycles in the field of drug development. In this work, a method via electrochemical decarboxylative cyclization of α-amino-oxy acids to access phenanthridine derivatives was developed. This reaction proceeded th
Gold Catalysts Can Generate Nitrone Intermediates from a Nitrosoarene/Alkene Mixture, Enabling Two Distinct Catalytic Reactions: A Nitroso-Activated Cycloheptatriene/Benzylidene Rearrangement
Cheng, Mu-Jeng,Kardile, Rahul Dadabhau,Kuo, Tung-Chun,Liu, Rai-Shung,More, Sayaji Arjun
, p. 5506 - 5511 (2021/07/31)
Gold-catalyzed reactions of cycloheptatrienes with nitrosoarenes yield nitrone derivatives efficiently. This reaction sequence enables us to develop gold-catalyzed aerobic oxidations of cycloheptatrienes to afford benzaldehyde derivatives using CuCl and nitrosoarenes as co-catalysts (10-30 mol %). Our density functional theory calculations support a novel nitroso-activated rearrangement, tropylium → benzylidene. With the same nitrosoarenes, we developed their gold-catalyzed [2 + 2 + 1]-annulations between nitrosobenzene and two enol ethers to yield 5-alkoxyisoxazolidines using 1,4-cyclohexadienes as hydrogen donors.
Base-Free Suzuki–Miyaura Coupling Reaction Using Palladium(II) Supported Catalyst in Water
Tomar, Ravi,Singh, Nidhi,Kumar, Neeraj,Tomar, Vartika,Chandra, Ramesh
, (2019/03/21)
Abstract: The carbon–carbon bond formation via Suzuki–Miyaura reaction was performed in water as green solvent. Pd(OAc)2(PPh3)2 supported on magnesium hydroxide and cerium carbonate hydroxide composite was prepared and characterized by various techniques. The cross-coupling reaction of aryl halides carried out in water using mild conditions. The effects of temperature, solvents, the amount of catalyst and leaving groups were studied to find the optimization conditions for cross-coupling reaction. Various aryl halides were smoothly transformed into the biaryls in good yields. In addition, the catalyst also exhibited stability and catalytic performance in the cross-coupling of aryl halides. Graphical Abstract: [Figure not available: see fulltext.] A new approach is developed for carbon–carbon bond formation via Suzuki–Miyaura reaction.2 Pd(OAc)2(PPh3)2?supported on mixed magnesium hydroxide and cerium carbonate hydroxide were prepared and characterized by XRD, XPS, SEM–EDX techniques. The cross-coupling reaction of aryl halides can be carried out in water and under mild conditions (80 °C).
Indolylbenzimidazole-based ligands catalyze the coupling of arylboronic acids with aryl halides
Wang, Meng-Pei,Chiu, Chien-Cheng,Lu, Ta-Jung,Lee, Dong-Sheng
, (2018/06/07)
A novel class of compounds bearing indole and benzimidazole rings was designed and easily synthesized from 2-indolecarboxylic acid and o-phenylenediamine. The catalytic system derived from a 2-indolylbenzimidazole-based ligand and Pd(OAc)2 in situ could lead to complete conversion of aryl bromides at 0.5?mol% Pd loading under mild reaction conditions. In the presence of a catalyst, sterically hindered biaryls were selectively generated in excellent yields by adjusting reaction parameters through the coupling of arylboronic acids with aryl halides. The efficiency of this reaction was demonstrated by its compatibility with various functional groups.
Amide-Directed C?H Sodiation by a Sodium Hydride/Iodide Composite
Huang, Yinhua,Chan, Guo Hao,Chiba, Shunsuke
supporting information, p. 6544 - 6547 (2017/05/29)
A new protocol for amide-directed ortho and lateral C?H sodiation is enabled by sodium hydride (NaH) in the presence of either sodium iodide (NaI) or lithium iodide (LiI). The transient organosodium intermediates could be transformed into functionalized aromatic compounds.
Atroposelective Synthesis of Axially Chiral Biaryls by Palladium-Catalyzed Asymmetric C?H Olefination Enabled by a Transient Chiral Auxiliary
Yao, Qi-Jun,Zhang, Shuo,Zhan, Bei-Bei,Shi, Bing-Feng
supporting information, p. 6617 - 6621 (2017/05/29)
Atroposelective synthesis of axially chiral biaryls by palladium-catalyzed C?H olefination, using tert-leucine as an inexpensive, catalytic, and transient chiral auxiliary, has been realized. This strategy provides a highly efficient and straightforward access to a broad range of enantioenriched biaryls in good yields (up to 98 %) with excellent enantioselectivities (95 to >99 % ee). Kinetic resolution of trisubstituted biaryls bearing sterically more demanding substituents is also operative, thus furnishing the optically active olefinated products with excellent selectivity (95 to >99 % ee, s-factor up to 600).
Silver-Catalyzed Tandem C=C Bond Hydroazidation/Radical Addition/Cyclization of Biphenyl Acetylene: One-Pot Synthesis of 6-Methyl Sulfonylated Phenanthridines
Tang, Jiawei,Sivaguru, Paramasivam,Ning, Yongquan,Zanoni, Giuseppe,Bi, Xihe
supporting information, p. 4026 - 4029 (2017/08/14)
A silver-catalyzed tandem carbon-carbon triple bond hydroazidation, radical addition, and cyclization of biphenyl acetylene is described under mild conditions, leading to the formation of 6-methyl sulfonylated phenanthridines in good yields. In this novel cascade reaction, most of the atoms are incorporated into the product without cleavage of the C=C bond. Mechanistic studies suggest the reaction should proceed through an iminyl radical reactive intermediate.
(Biphenyl-2-alkyne) derivatives as common precursors for the synthesis of 9-iodo-10-organochalcogen-phenanthrenes and 9-organochalcogen-phenanthrenes
Grimaldi, Tamiris B.,Lutz, Guilherme,Back, Davi F.,Zeni, Gilson
, p. 10415 - 10426 (2016/11/18)
In this paper, we report our results on the cyclization of (biphenyl-2-alkyne) derivatives to give two different types of phenanthrene derivatives, 9-iodo-10-organochalcogen-phenanthrenes and 9-organochalcogen-phenanthrenes. The strategy for the synthesis was based on the use of electrophilic cyclization for the preparation of 9-iodo-10-organochalcogen-phenanthrenes and iron(iii) chloride/diorganyl diselenide-mediated intramolecular cyclization to prepare 9-organochalcogen-phenanthrenes. The effects of solvent, temperature, reaction time and stoichiometry on the efficiency of cyclization reactions were investigated. The standard reaction conditions were compatible with many functional groups in the substrates, such as methyl, chlorine, fluorine and methoxyl. This protocol was efficient for diorganyl diselenides and disulfides but ineffective for diorganyl ditellurides. The resulting phenanthrenes were further functionalized through Sonogashira reactions followed by the electrophilic cyclization reaction to give the selenophene-fused aromatic compounds.
Rapid threefold cross-couplings with sterically bulky triarylbismuths under Pd-Cu dual catalysis
Rao, Maddali L. N.,Dhanorkar, Ritesh J.
, p. 1012 - 1017 (2016/01/16)
The threefold cross-coupling reactivity of sterically highly demanding bulky triarylbismuths was addressed with task specific Pd-Cu dual catalytic conditions. In this study, an unprecedented hitherto unknown cross-coupling reactivity of sterically bulky triarylbismuths was demonstrated with a diverse range of aryl iodides and bromides. The intermediacy and in situ formation of arylcopper was probed with mesitylcopper in support of the proposed dual catalysis. This study opened up an easy way forward for application of sterically bulky bismuth reagents in threefold aryl-aryl coupling reactions.
Copper catalyzed room temperature lactonization of aromatic C-H bond: A novel and efficient approach for the synthesis of dibenzopyranones
Singha, Raju,Dhara, Shubhendu,Ghosh, Munmun,Ray, Jayanta K.
, p. 8801 - 8805 (2015/03/03)
We have developed a novel and efficient methodology for the intramolecular aryl C-H oxidative lactonization of 2-arylbenzaldehyde using a low-cost CuCl catalyst and TBHP as the oxidant at room temperature. We applied the methodology to the synthesis of a series of dibenzopyranones.
