28861-22-5Relevant academic research and scientific papers
"on water" palladium catalyzed diastereoselective boronic acid addition to structurally diverse cyclopropane nitriles
Das, Asish R.,Das, Dwaipayan,Mukherjee, Prasun
, p. 8886 - 8898 (2020)
An efficient palladium catalyzed diastereoselective addition of arylboronic acids to complex spirocyclopropyl dinitriles is developed in the presence of a catalytic amount of 4-dodecylbenzenesulphonic acid (DBSA) as a Br?nsted acid surfactant in aqueous media. The protocol is also found to be highly effective when different types of nitrile compounds and organo-boron compounds are used. The overall reaction has been found to be very cost efficient since it requires low catalyst loading, mild thermal energy and short reaction time. Wide substrate scope, operational simplicity, good to excellent product yield, and use of green solvents make the reaction a practical route to transform nitrile into a keto functionality in biorelevant heterocyclic scaffolds. The scale-up synthesis of the target scaffolds can also be achieved with ease which also signifies the practicability of this protocol. This journal is
The Formation of C-C or C-N Bonds via the Copper-Catalyzed Coupling of Alkylsilyl Peroxides and Organosilicon Compounds: A Route to Perfluoroalkylation
Xu, Weiping,Liu, Yan,Kato, Terumasa,Maruoka, Keiji
, p. 1809 - 1813 (2021/04/05)
The copper-catalyzed selective cleavage of alkylsilyl peroxides and the subsequent formation of carbon-carbon or carbon-nitrogen bonds with organosilicon compounds are described. The reaction proceeds under mild conditions and exhibits a broad substrate scope with respect to both cyclic and acyclic alkylsilyl peroxides in combination with carbon and nitrogen sources. In particular, this approach enables the facile radical perfluoroalkylation using commercially available perfluoroalkyltrimethylsilanes. Our mechanistic studies suggest that the reaction should proceed via a free-radical process.
Syntheses of Pyrroles, Pyridines, and Ketonitriles via Catalytic Carbopalladation of Dinitriles
Qi, Linjun,Li, Renhao,Yao, Xinrong,Zhen, Qianqian,Ye, Pengqing,Shao, Yinlin,Chen, Jiuxi
supporting information, p. 1097 - 1108 (2020/01/22)
The first example of the Pd-catalyzed addition of organoboron reagents to dinitriles, as an efficient means of preparing 2,5-diarylpyrroles and 2,6-diarylpyridines, has been discussed here. Furthermore, the highly selective carbopalladation of dinitriles with organoboron reagents to give long-chain ketonitriles has been developed as well. Based on the broad scope of substrates, excellent functional group tolerance, and use of commercially available substrates, the Pd-catalyzed addition reaction of arylboronic acid and dinitriles is expected to be significant in future synthetic procedures.
Tailoring flavins for visible light photocatalysis: organocatalytic [2+2] cycloadditions mediated by a flavin derivative and visible light
Mojr, Viktor,Svobodová, Eva,Straková, Karolína,Nevesely, Tomá?,Chudoba, Josef,Dvo?áková, Hana,Cibulka, Radek
supporting information, p. 12036 - 12039 (2015/07/28)
A new application of flavin derivatives in visible light photocatalysis was found. 1-Butyl-7,8-dimethoxy-3-methylalloxazine, when irradiated by visible light, was shown to allow an efficient cyclobutane ring formation via an intramolecular [2+2] cycloaddition of both styrene dienes, considered as electron-rich substrates, and electron-poor bis(arylenones), presumably proceeding via an energy transfer mechanism.
Anodic cyclization of 1,7-diarylheptane-1,7-diones to the corresponding 1,2-diaroylcyclopentanes
Okimoto, Mitsuhiro,Yamamori, Haruki,Ohashi, Kousuke,Nishikawa, Shinnosuke,Hoshi, Masayuki,Yoshida, Takashi
, p. 2544 - 2548,5 (2012/12/11)
A range of 1,7-diarylheptane-1,7-diones were electrooxidized in the presence of iodide ions and a base in a mixture of methanol and toluene as the reaction solvents to give the corresponding cyclized 1,2-diaroylcyclopentanes in moderate to good yields. Th
Anodic cyclization of 1,7-diarylheptane-1,7-diones to the corresponding 1,2-diaroylcyclopentanes
Okimoto, Mitsuhiro,Yamamori, Haruki,Ohashi, Kousuke,Nishikawa, Shinnosuke,Hoshi, Masayuki,Yoshida, Takashi
, p. 2544 - 2548 (2013/01/13)
A range of 1,7-diarylheptane-1,7-diones were electrooxidized in the presence of iodide ions and a base in a mixture of methanol and toluene as the reaction solvents to give the corresponding cyclized 1,2-diaroylcyclopentanes in moderate to good yields. Th
Molecular engineering of the glass transition: Glass-forming ability across a homologous series of cyclic stilbenes
Ping, Wen,Paraska, Daniel,Baker, Robert,Harrowell, Peter,Angell, C. Austen
body text, p. 4696 - 4702 (2011/06/09)
We report on the glass-forming abilities of the homologous series 1,2-diphenylcyclo-butene, pentene, hexene and heptene-a series that retains the cis-phenyl configuration characteristic of the well-studied glass former, o-terphenyl. We find that the glass
Synthesis and structure of 1-methyl-2,6-bis(electron-withdrawing group)-substituted selenabenzenes
Honda, Eiji,Iwamura, Tatsunori,Watanabe, Shin-Ichi,Kataoka, Tadashi,Muraoka, Osamu,Tanabe, Genzoh
, p. 529 - 536 (2007/10/03)
The synthesis and structure of 1-methyl-2,6-bis(electron-withdrawing group)-substituted selenabenzenes from dihalides was presented. The monocyclic selenabenzene derivatives stabilized by two electron withdrawing groups at the 2- and 6-positions were isolated. The x-ray structural analysis of the dibenzoyl derivatives showed that the six-membered ring containing a selenium atom is planar and the structure of selenium atom is tetrahedral with four sp3 hybridized orbitals.
Effects of methylene chains on photoreactions of diphenylalkanediones and phenylalkenones
Nakamura, Mitsunobu,Miki, Masamichi,Majima, Tetsuro
, p. 415 - 420 (2007/10/03)
Upon conventional UV-irradiation of I,ω-diphenylalkane-1,ω-dione (PhC(O)-(CH2)n-C(O)Ph, n= 5, 6, 7, 8, and 10) in acetonitrile using a medium-pressure Hg lamp, an intramolecular γ-hydrogen abstraction of the triplet ketone (type II p
Lewis Acid-Promoted Disproportionation Reaction of Aromatic Vinyl Ethers and Acetals and Its Application to the Synthesis of Paracotoin
Gong, Young Dae,Tanaka, Hiroko,Iwasawa, Nobuharu,Narasaka, Koichi
, p. 2181 - 2185 (2007/10/03)
Aromatic vinyl ethers and acetals underwent a novel addition-fragmentation reaction affording olefins and esters in the presence of a Lewis acid. This reaction was applied to intramolecular cyclization reaction, giving five or six membered ring compounds in good yields. Paracotoin, an intermediate in the biosynthesis of shikimic acid, was synthesized using this cyclization reaction as the key step.
