269066-75-3Relevant articles and documents
Pd(0)-catalyzed intramolecular Heck reaction: A general route for fused oxepine derivatives
Adak, Arup Kumar,Mandal, Arabinda,Manna, Susanta Kumar,Mondal, Suresh Kumar,Jana, Akash,Ghosh, Dipesh,Kundu, Debasish,Samanta, Shubhankar,Ray, Jayanta K.
, p. 452 - 459 (2016)
A simple and facile approach for the synthesis of various structurally different tricyclic bent oxepine frameworks from a readily accessible precursor has been introduced. The synthesis of substituted oxepine derivative involved Pd(0)-catalyzed Heck reaction. This methodology enriches the literature for the large ring formation.
Palladium-Catalyzed Regiospecific peri- And ortho-C-H Oxygenations of Polyaromatic Rings Mediated by Tunable Directing Groups
Hu, Lihong,Jiang, Jing,Lin, Yaoyu,Ma, Congzhe,Song, Wanbin,Yuan, Dandan,Zhang, Yinan
, p. 279 - 284 (2021/01/13)
An efficient divergent approach of Pd-catalyzed C-H oxygenation of polyaromatic rings is described. Reversible directing groups enable regiospecific peri- and ortho-oxygenation to readily access a wide array of polyaromatic phenols without pre- and postmanipulation of directing groups. The systematic mechanistic investigation, including deuterium-labeling experiments, palladacycle trapping, and DFT calculations, reveals that the tunable ligand-assisted C-H bond cleavage played a crucial role during the reaction process.
NHC-Catalyzed Synthesis of Benzazole-Phosphine Ligands under an Air Atmosphere
Ren, Wei,Yang, Shang-Dong,Zuo, Qian-Ming
, p. 1719 - 1724 (2019/08/28)
An efficient strategy for the synthesis of benzazole-phosphine ligand precursors via N -heterocyclic carbene catalyzed aerobic oxidative cyclization reaction has been performed. The reaction displays broad functional group tolerance and high atom economy,
A Strategy To Obtain o-Naphthoquinone Methides: Ag(I)-Catalyzed Cyclization of Enynones for the Synthesis of Benzo[ h]chromanes and Naphthopyryliums
Wu, Feng,Zhu, Shifa
, (2019/03/08)
A new strategy to obtain o-NQM intermediates through a ring-formation strategy by Ag(I)-catalyzed cyclization of 2-alkenylphenyl alkynyl ketones and its [4 + 2] annulations with styrenes has been developed. This reaction features high efficiency, mild reaction conditions, as well as flexible substitutions and atom economy. The obtained benzo[h]chromane products were further oxidized to naphthopyryliums, which displayed tunable photophysical properties.
Mechanistic studies of hoveyda-grubbs metathesis catalysts bearing S-, Br-, I-, and N-coordinating naphthalene ligands
Grudzien, Krzysztof,Zukowska, Karolina,Malinska, Maura,Wozniak, Krzysztof,Barbasiewicz, Michal
supporting information, p. 2819 - 2828 (2014/03/21)
Derivatives of the Hoveyda-Grubbs complex bearing S-, Br-, I-, and N-coordinating naphthalene ligands were synthesized and characterized with NMR and X-ray studies. Depending on the arrangement of the coordinating sites on the naphthalene core, the isomeric catalysts differ in activity in model metathesis reactions. In particular, complexes with the Rui￡CH bond adjacent to the second aromatic ring of the ligand suffer from difficulties experienced on their preparation and initiation. The behavior most probably derives from steric hindrance around the double bond and repulsive intraligand interactions, which result in abnormal chemical shifts of benzylidene protons observed with 1HNMR. Furthermore EXSY studies revealed that the halogen-chelated ruthenium complexes display an equilibrium, in which major cis-Cl2 structures are accompanied with small amounts of isomeric forms. In general, contents of the minor forms, measured at 80°C, correlate with the observed activity trends of the catalysts, although some exceptions complicate the mechanistic picture. We assume that for the family of halogen-chelated metathesis catalysts the initiation mechanism starts with the cis-Cl 2a?trans-Cl2 isomerization, although further steps may become rate-limiting for selected systems. Isomerization first: A family of halogen-chelated Hoveyda-Grubbs complexes displays a cis-Cl2a?trans-Cl2 equilibrium in solution. Relative contents of the minor trans forms go along with the activity of the metathesis catalysts, suggesting its participation in the initiation mechanism (see figure). A unique effect of the naphthalene ligands enables control of the activity over a broad range, from moderately achieve to dormant, and was manifested in 1HNMR for complexes with repulsive H×××H intraligand interactions (Mes=Mesityl).
Copper(I) salt/PEG-400 catalysis in one-pot direct synthesis of 1-aryl-1H-indazoles from 2-bromobenzaldehydes and arylhydrazines
Bae, Yeon Kyu,Cho, Chan Sik
, p. 224 - 227 (2013/05/23)
2-Bromobenzaldehydes are condensed and cyclized with arylhydrazines (or their hydrochlorides) in PEG-400 at 110 °C in the presence of a catalytic amount of a copper(I) salt along with a base to give 1-aryl-1H-indazoles in high yields. Copyright 2013 John Wiley & Sons, Ltd. Condensation of 2-bromobenzaldehydes with arylhydrazines (or their hydrochlorides) followed by C-N bond formation in PEG-400 in the presence of a copper(I) salt along with a base affords 1-aryl-1H-indazoles. Copyright
Structure-property relationship of naphthalene based donor-π-acceptor organic dyes for dye-sensitized solar cells: Remarkable improvement of open-circuit photovoltage
Yang, Fan,Jin, Tienan,Yamamoto, Yoshinori,Akhtaruzzaman, Md.,Islam, Ashraful,Qin, Chuanjiang,Han, Liyuan,El-Shafei, Ahmed,Alamry, Khalid A.,Kosa, Samia A.,Hussein, Mahmoud A.,Asiri, Abdullah Mohamed
supporting information, p. 22550 - 22557,8 (2020/09/15)
Four new donor-π-acceptor organic dyes (YF01-04), containing naphthalene-substituted amines as an electron donor and cyanoacrylic acid as an electron acceptor, were designed and synthesized, and their photophysical properties and dye-sensitized solar cells (DSCs) performances were characterized. Dyes YF02 and YF04, with 2,6-disubstituted naphthalene frameworks, were superior than their analog dyes YF03 and YF01, having 1,2-disubstituted naphthalene moiety, in incident-photo-to-current conversion efficiency (IPCE) and total solar-to-electric conversion efficiency (η). The DSCs based on YF02, comprised of diphenylamine moiety as the donor, produced the highest η of 5.29% compared to 4.03% of the analog dye YF04, which has pyrrolidine as the donor. Remarkably, a high open-circuit photovoltage (V oc) of 0.799-0.807 V was achieved in the cases of YF02-03, which have diphenylamine-donors. To better understand the structure-property relationship for DSCs application, molecular modelling was performed on YF01-04 and vertical electronic excitations were calculated using long-range corrected energy functional WB97XD and CAM-B3LYP at the basis set level DGDZVP, which were in excellent agreement with the experimental results. Moreover, the equilibrium molecular geometries of dyes YF01-04 were calculated at the density function theory (DFT) level using the hybrid energy functional B3LYP and basis set DGDZVP. The torsion angles () between the naphthalene moiety and diphenylamine donor in YF02 and YF03 were more twisted than that of the pyrrolidine-donor dyes YF01 and YF04, precluding efficient intermolecular π-π charge transfer, which translated into high Voc. Compared to the reference dye TA-St-CA, which is based on diphenylamine as an electron donor linked to a phenyl ring, YF02 achieved higher Voc, which indicated that naphthalene substituted with diphenylamine is more efficient in retarding charge recombinations.
Palladium-catalyzed intramolecular C-H activation: A synthetic approach towards polycyclic aromatic hydrocarbons
Paul, Sunanda,Jana, Rathin,Ray, Jayanta K.
scheme or table, p. 1463 - 1468 (2010/08/20)
A simple and convenient synthetic protocol for the construction of polycyclic aromatic hydrocarbons has been developed. A variety of phenanthrene, benzo[c]phenanthrene and chrysene derivatives was synthesized via Pd-catalyzed intramolecular C-H activation followed by acid-catalyzed water elimination.
Palladium-catalyzed one-pot Suzuki coupling followed by arylpalladium addition to aldehyde: A convenient route to fluoren-9-one derivatives
Paul, Sunanda,Samanta, Shubhankar,Ray, Jayanta K.
scheme or table, p. 5604 - 5608 (2010/10/21)
Various fluoren-9-one derivatives were prepared efficiently by a one-pot reaction involving sequential Suzuki coupling of 2-bromophenyl boronic acid with 2-bromocarboxaldehyde followed by intramolecular arylpalladium addition to aldehyde.
Studies on polynuclear furoquinones. Part 1: Synthesis of tri- and tetra-cyclic furoquinones simulating BCD/ABCD ring system of furoquinone diterpenoids
Shaik, Faruk H.,Kar, Gandhi K.
supporting information; experimental part, (2010/04/22)
Synthesis of phenanthro[1,2-b]furan-10,11-dione, the core nucleus present in Tanshinone-I is described in 8-10 steps starting from 2-bromo-3,4-dihydro-1- naphthaldehyde. The bromoaldehyde was converted to methyl 2-(2-bromo-1-naphthyl) acetate or 2-(2- bro
