78602-28-5Relevant academic research and scientific papers
Br?nsted Acid-Catalyzed Carbonyl-Olefin Metathesis: Synthesis of Phenanthrenes via Phosphomolybdic Acid as a Catalyst
Chen, Yi,Liu, Di,Wang, Rui,Xu, Li,Tan, Jingyao,Shu, Mao,Tian, Lingfeng,Jin, Yuan,Zhang, Xiaoke,Lin, Zhihua
supporting information, p. 351 - 362 (2022/01/03)
Compared with the impressive achievements of catalytic carbonyl-olefin metathesis (CCOM) mediated by Lewis acid catalysts, exploration of the CCOM through Br?nsted acid-catalyzed approaches remains quite challenging. Herein, we disclose a synthetic protocol for the construction of a valuable polycycle scaffold through the CCOM with the inexpensive, nontoxic phosphomolybdic acid as a catalyst. The current annulations could realize carbonyl-olefin, carbonyl-alcohol, and acetal-alcohol in situ CCOM reactions and feature mild reaction conditions, simple manipulation, and scalability, making this strategy a promising alternative to the Lewis acid-catalyzed COM reaction.
Palladium Nanoparticles Supported on Cellulosic Paper as Multifunctional Catalyst for Coupling and Hydrogenation Reactions
Kalanthoden, Abdul Nasar,Zahir, Md. Hasan,Aziz, Md. Abdul,Al-Najar, Basmah,Rani, S. Kutti,Shaikh, M. Nasiruzzaman
, (2022/01/06)
Hallmark of a successful catalyst is its high efficiency, economic aspects, operational simplicity, extensive reusability, higher environment friendliness, and potential use in multiple industrial applications. Herein, a facile protocol involving a cataly
Quaternary Phosphonium Carboxylates: Structure, Dynamics and Intriguing Olefination Mechanism
Müller-Bunz, Helge,Muldoon, Jimmy,Nikitin, Kirill,Vetter, Anna C.
supporting information, (2022/01/12)
We have earlier shown how the Wittig chemistry can be done using novel Eigenbase phosphonium carboxylate reagents. Here we discuss the phenomenon of ion pairing, their solution tautomerism, solid-state structure, and mechanistic aspects of olefination. The results point to a complex process involving unfamiliar H-bond-driven ion-pair equilibria followed by standard Wittig reaction steps.
Catalytic Systems for Production of 1-Hexene by Selective Ethylene Trimerization
Afanas’ev, V. V.,Bespalova, N. B.,Cheredilin, D. N.,Kozlova, G. A.,Senin, A. A.,Sheloumov, A. M.
, p. 55 - 68 (2020/02/25)
Abstract: New chromium complexes with diphosphine ligands have been obtained by the reaction of chromium(III) hexahydrate and diphosphines in acetone. The structure of chromium(III) complex 4 containing water molecule and 1,2-bis(diphenylphosphino)benzene as ligands and that of two chromium(III) complexes (12 and 13) with 1,2-bis(diphenylphosphino)benzene ligands containing alkenyl substituents in the ortho-position of one of the phenyl groups at the phosphorous atom have been determined using X-ray diffraction analysis. The catalytic properties of the obtained complexes in the composition of catalytic systems for ethylene trimerization have been studied. It has been shown that the obtained series of catalytic systems manifests high activity in the process of ethylene trimerization to 1-hexene, with the process selectivity exceeding 94%. The highest value of productivity amongst known selective catalytic systems for trimerization was achieved using a chromium complex 13 bearing the 2-methylprop-1-enyl group at the ortho-position of one of the phenyl groups. The influence of temperature, pressure, the nature of the solvent and the composition of the catalytic system on the parameters of the process of ethylene trimerization to form 1-hexene has been determined.
Tailoring Diindenochrysene through Intramolecular Multi-Assemblies by C?F Bond Activation on Aluminum Oxide
Akhmetov, Vladimir,Feofanov, Mikhail,Troyanov, Sergey,Amsharov, Konstantin
supporting information, p. 7607 - 7612 (2019/05/15)
The unique nature of the alumina-mediated cyclodehydrofluorination gives the opportunity to execute the preprogrammed algorithm of the C?C couplings rationally built into a precursor. Such multi-assemblies facilitate the construction of the carbon-skeleton, superseding the conventional step-by-step by the one-pot intramolecular assembly. In this work, the feasibility of the alumina-mediated C?F bond activation approach for multi-assembly is demonstrated on the example of a fundamental bowl-shaped polycyclic aromatic hydrocarbon (diindenochrysene) through the formation of all “missing” C?C bonds at the last step. Beside valuable insights into the reaction mechanism and the design of the precursors, a facile pathway enabling the two-step synthesis of diindenochrysene was elaborated, in which five C?C bonds form in a single synthetic step. It is shown that the relative positions of fluorine atoms play a crucial role in the outcome of the assembly and that governing the substituent positions enables the design of effective precursor molecules “programmed” for the consecutive C?C bond formations. In general, these findings push the state of the field towards the facile synthesis of sophisticated bowl-shaped carbon-based nanostructures through multi-assembly of fluoroarenes.
Strategy for Overcoming Full Reversibility of Intermolecular Radical Addition to Aldehydes: Tandem C-H and C-O Bonds Cleaving Cyclization of (Phenoxymethyl)arenes with Carbonyls to Benzofurans
Zheng, Hong-Xing,Shan, Xiang-Huan,Qu, Jian-Ping,Kang, Yan-Biao
, p. 3310 - 3313 (2018/06/11)
An intermolecular addition of carbon radicals enabled by a cascade radical coupling strategy is developed. It includes an intermolecular alkyl radical addition to a carbonyl group followed by an intramolecular alkoxy radical addition to haloarenes and produces substituted benzofurans in high yields. The radical nature of this reaction is explored by radical trapping experiments and EPR analysis. The mechanism is investigated by KIE experiments and control experiments. This method could provide rapid and practical access to the key intermediate of TAM-16, a safe and potent antibacterial agent for treating tuberculosis, and, therefore, is of great importance for organic synthesis and the pharmaceutical industry.
Hf(OTf)4-Catalyzed highly diastereoselective synthesis of 1,3-disubstituted tetralin derivatives via benzylic C(sp3)-H bond functionalization
Yoshida, Taira,Mori, Keiji
supporting information, p. 4319 - 4322 (2017/04/21)
We report a highly diastereoselective synthesis of 1,3-disubstituted tetralin derivatives via Lewis acid catalyzed benzylic C(sp3)-H bond functionalization. The employment of Hf(OTf)4 as an acid catalyst was crucial in the reaction,
Magnetic nanoparticle-supported ferrocenylphosphine: A reusable catalyst for hydroformylation of alkene and Mizoroki-Heck olefination
Shaikh, M. Nasiruzzaman,Aziz, Md. Abdul,Helal, Aasif,Bououdina, Mohamed,Yamani, Zain H.,Kim, Tae-Jeong
, p. 41687 - 41695 (2016/05/19)
We present dopamine (dop) conjugated bis(diphenylphosphino)ferrocenylethylamine (BPPFA) functionalized magnetic nanoparticles (Fe3O4). A ferrocene ({η5-C5H4-PPh2}Fe{η5-C5H3-1-PPh2-2-CH(Me)NH-CH2-CH2-4Ph-1,2-OH}) ligand (dop-BPPF) has been prepared by reaction of (1-[1′,2-bis(diphenylphosphino)-ferrocenyl]ethyl acetate) and dopamine hydrochloride to form dop-BPPF, which was characterized by NMR, IR, FTIR, EA and FAB-MS. This ligand was anchored on ultrasmall (6-8 nm) magnetic nanoparticles (MNP) to yield Fe3O4@dop-BPPF. The resulting ferrocenylphosphine on magnetic nanoparticles was characterized by SEM, EDS, XRD, TEM, TGA, and VSM. The magnetic nature of the materials was investigated. Fe3O4@dop-BPPF exhibits very high catalytic activity for the Pd-catalyzed Mizoroki-Heck reaction and exceptionally high regioselectivity for the Rh-catalyzed hydroformylation reaction with branched aldehydes (up to > 99%). The potential of this Fe3O4@dop-BPPF as a reusable catalyst has been studied for the Mizoroki-Heck reaction, and this catalyst was robustly active even after eleven consecutive cycles.
Catalytic enantioselective C(sp3)H functionalization: Intramolecular benzylic [1,5]-hydride shift
Yu, Jie,Li, Nan,Chen, Dian-Feng,Luo, Shi-Wei
supporting information, p. 2859 - 2864 (2014/05/06)
The catalytic asymmetric [1,5]-hydride transfer/cyclization sequence involving benzylic C(sp3)H bond was established, providing tetrahydronaphthalene derivatives in moderate to high yield with up to 69% ee, by employing the copper complex of si
Transition-metal-free method for the synthesis of benzo[b]thiophenes from o -halovinylbenzenes and K2S via direct SNAr-type reaction, cyclization, and dehydrogenation process
Zhang, Xiaoyun,Zeng, Weilan,Yang, Yuan,Huang, Hui,Liang, Yun
, p. 1687 - 1692 (2013/09/02)
A new, highly efficient procedure for the synthesis of benzothiophenes from easily available o-halovinylbenzenes and potassium sulfide has been developed. The reaction tolerated a wide range of functionalities, and various 2-substituted benzo[b]thiophenes
