78210-35-2Relevant academic research and scientific papers
Pd-catalyzed protecting-group-free cross-couplings of iodophenols with atom-economic triarylbismuth reagents
Rao, Maddali L.N.,Meka, Suresh
, (2019/12/30)
An efficient protocol for the protecting-group-free synthesis of unsymmetrical hydroxybiaryls via the Pd-catalyzed cross-couplings of unprotected iodophenols with triarylbismuth reagents is described. The presented protocols exhibits good to high yields of hydroxybiaryls.
Chemoselective Borono-Catellani Arylation for Unsymmetrical Biaryls Synthesis
Wang, Peng,Chen, Shuqing,Zhou, Zhiyu,Cheng, Hong-Gang,Zhou, Qianghui
supporting information, p. 3323 - 3327 (2019/05/10)
Reported is the borono-Catellani arylation process for unsymmetrical biaryls synthesis, utilizing the readily available pinacol ester of arylboronic acids, aryl bromides, and olefins as the reactants. The distinct reactivity of arylboronic ester and aryl bromides secures the excellent chemoselectivity in the pivotal arylation step. The reaction is enabled by the cooperative catalysis of Pd(OAc)2 and the NBE derivative N7, with molecular oxygen as the terminal oxidant.
Towards identifying potent new hits for glioblastoma
Sherer, Chris,Prabhu, Saurabh,Adams, David,Hayes, Joseph,Rowther, Farzana,Tolaymat, Ibrahim,Warr, Tracy,Snape, Timothy J.
, p. 1850 - 1861 (2018/11/24)
Glioblastoma is a devastating disease of the brain and is the most common malignant primary brain tumour in adults. The prognosis for patients is very poor with median time of survival after diagnosis measured in months, due in part to the tumours being highly aggressive and often resistant to chemotherapies. Alongside the ongoing research to identify key factors involved in tumour progression in glioblastoma, medicinal chemistry approaches must also be used in order to rapidly establish new and better treatments for brain tumour patients. Using a computational similarity search of the ZINC database, alongside traditional analogue design by medicinal chemistry intuition to improve the breadth of chemical space under consideration, six new hit compounds (14, 16, 18, 19, 20 and 22) were identified possessing low micromolar activity against both established cell lines (U87MG and U251MG) and patient-derived cell cultures (IN1472, IN1528 and IN1760). Each of these scaffolds provides a new platform for future development of a new therapy in this area, with particular promise shown against glioblastoma subtypes that are resistant to conventional chemotherapeutic agents.
An acetatopalladium(II) complex with 1-benzyl-N-(3,5-di-tert-butylsalicylidene)piperidin-4-amine: Synthesis, structure and catalytic applications in Suzuki–Miyaura coupling of arylboronic acids with hydroxyaryl halides
Keesara, Srinivas,Narendra Babu,Pal, Samudranil
, (2017/09/30)
The Schiff base 1-benzyl-N-(3,5-di-tert-butylsalicylidene)piperidin-4-amine (HL) and its acetatopalladium(II) complex having the formula [Pd(L)(OAc)] were synthesized. Both HL and [Pd(L)(OAc)] were characterized using elemental analysis and various spectroscopic (infrared, UV–visible, 1H NMR and 13C NMR) and mass spectrometric measurements. The molecular structure of the complex was determined using X-ray crystallographic analysis. In the complex, the pincer-like NNO-donor L? and the monodenate OAc? provide a distorted square-planar N2O2 coordination environment around the metal centre. The physicochemical properties and the spectroscopic features of [Pd(L)(OAc)] are consistent with its molecular structure. The complex was found to be an effective catalyst for the Suzuki–Miyaura cross-coupling reactions of hydroxyaryl halides with arylboronic acids in predominantly aqueous media. The reactions afforded hydroxybiaryl products in good to excellent yields with a wide substrate scope.
Microwave-Promoted Pd-Catalyzed Synthesis of Dibenzofurans from Ortho-Arylphenols
Schmidt, Bernd,Riemer, Martin
, p. 1287 - 1297 (2017/03/27)
ortho-Aryl phenols, synthesized via protecting group free Suzuki–Miyaura coupling of ortho-halophenols and arene boronic acids, undergo a cyclization to dibenzofurans via oxidative C–H activation. The reaction proceeds under microwave irradiation in short reaction times using catalytic amounts of Pd(OAc)2 without additional ligands.
Synthesis of 2,2′-biphenols through direct C(sp2)-H hydroxylation of [1,1′-biphenyl]-2-ols
Duan, Shitao,Xu, Yuanshuang,Zhang, Xinying,Fan, Xuesen
supporting information, p. 10529 - 10532 (2016/09/02)
A novel synthesis of diversely substituted 2,2′-biphenols through Pd(ii)-catalyzed, tBuOOH-oxidized, and hydroxyl-directed C(sp2)-H hydroxylation of [1,1′-biphenyl]-2-ols has been developed. Notably, this finding is distinct from previous reports in which [1,1′-biphenyl]-2-ols underwent an intramolecular C-H activation and C-O bond formation to afford dibenzofurans under the promotion of Pd(ii) but in the absence of tBuOOH.
Excited state intramolecular proton transfer (ESIPT) from phenol to carbon in selected phenylnaphthols and naphthylphenols
Basari?, Nikola,Do?li?, Nacrossed D Signa,Ivkovi?, Jakov,Wang, Yu-Hsuan,Veljkovi?, Jelena,Mlinari?-Majerski, Kata,Wan, Peter
, p. 1811 - 1823 (2013/04/10)
ESIPT and solvent-assisted ESPT in isomeric phenyl naphthols and naphthyl phenols 5-8 were investigated by preparative photolyses in CH 3CN-D2O, fluorescence spectroscopy, LFP, and ab initio calculations. ESIPT takes place only in 5 (D-exchange Φ = 0.3), whereas 6-8 undergo solvent-assisted PT with much lower efficiencies. The efficiency of the ESIPT and solvent-assisted PT is mainly determined by different populations of the reactive conformers in the ground state and the NEER principle. The D-exchange experiments and calculations using RI-CC2/cc-pVDZ show that 5 in S1 deactivates by direct ESIPT from the OH to the naphthalene position 1 through a conical intersection with S0, delivering QM 14 that was detected by LFP (τ = 26 ± 3 ns). ESIPT to position 3 in 5 is possible but it proceeds from a less-populated conformer and involves an energy barrier on S1. In solvent-assisted PT to naphthalene position 4 in 5, zwitterion 17 is formed, which cyclizes to stable naphthofuran photoproducts 9-12. The regiochemistry of the deuteration in solvent-assisted PT was correlated with the NBO charges of the corresponding phenolates/naphtholates 5--8-. Combined experimental and theoretical data indicate that solvent-assisted PT takes place via a sequential mechanism involving first deprotonation of the phenol/naphthol, followed by the protonation by H 2O in the S1 state of phenolate/naphtholate. The site of protonation by H2O is mostly at the naphthalene α-position.
Synthesis of dibenzopyranones through palladium-catalyzed directed C-H activation/carbonylation of 2-arylphenols
Luo, Shuang,Luo, Fei-Xian,Zhang, Xi-Sha,Shi, Zhang-Jie
supporting information, p. 10598 - 10601 (2013/10/21)
Dibenzopyranones were synthesized by a palladium-catalyzed phenol-directed C-H activation/carbonylation of 2-phenylphenol derivatives in the presence of CO. Pd(OAc)2 was used as a catalyst and Cu(OAc)2 as a catalytic oxidant in the presence of air. Copyright
Chromium- and tungsten-triggered valence isomerism of cis-1-acyl-2-ethynylcyclopropanes via [3,3] sigmatropy of (2-acylcyclopropyl)vinylidene - Metal intermediates
Ohe, Kouichi,Yokoi, Tomomi,Miki, Koji,Nishino, Fumiaki,Uemura, Sakae
, p. 526 - 527 (2007/10/03)
The reaction of cis vicinal acetylethynylcyclopropanes 1 with a catalytic amount of M(CO)5(THF) (M = Cr or W) in the presence of Et3N at room temperature gave ortho-substituted phenols 7 in good yields as valence isomerized products. In the absence of Et3N the reactions did not work at all. The reaction of a cyclopropane having an ester or an amide instead of an acetyl moiety with M(CO)5(THF) did not take place, whereas an ethynylvinylcyclopropane gave a mixture of 1- and 2-substituted 1,3,5-cycloheptatrienes. These valence isomerization reactions are assumed to proceed via the formation of vinylidene-metal intermediates 2 from terminal alkynyl moieties followed by [3,3]sigmatropy of 2 to give seven-membered carbene complexes 3. Copyright
