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613-37-6 Usage

Chemical Properties

white powder

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 1060, 1995 DOI: 10.1021/jo00109a044

Check Digit Verification of cas no

The CAS Registry Mumber 613-37-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 3 respectively; the second part has 2 digits, 3 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 613-37:
(5*6)+(4*1)+(3*3)+(2*3)+(1*7)=56
56 % 10 = 6
So 613-37-6 is a valid CAS Registry Number.
InChI:InChI=1/C13H12O/c1-14-13-9-7-12(8-10-13)11-5-3-2-4-6-11/h2-10H,1H3

613-37-6 Well-known Company Product Price

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  • Alfa Aesar

  • (L01260)  4-Methoxybiphenyl, 98+%   

  • 613-37-6

  • 5g

  • 240.0CNY

  • Detail
  • Alfa Aesar

  • (L01260)  4-Methoxybiphenyl, 98+%   

  • 613-37-6

  • 25g

  • 792.0CNY

  • Detail

613-37-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Methoxybiphenyl

1.2 Other means of identification

Product number -
Other names 1,1‘-Biphenyl, 4-methoxy-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

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Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:613-37-6 SDS

613-37-6Relevant articles and documents

Structure-activity relationship of N-heterocyclic carbene-Pd(II)-imidazole complexes in Suzuki-Miyaura coupling between 4-methoxyphenyl chloride and phenylboronic acid

Lv, Huan,Zhu, Lei,Tang, Yi-Qiang,Lu, Jian-Mei

, p. 27 - 31 (2014)

A series of N-heterocyclic carbene-PdCl2-imidazole [NHC-Pd(II)-Im] complexes were synthesized and the structure of most of them was unambiguously determined by X-ray single-crystal diffraction. The structure-activity relationship of these complexes was investigated for the Suzuki-Miyaura coupling between 4-methoxyphenyl chloride and phenylboronic acid, and the effect of the NHCs and Im moieties were fully discussed. The sterically hindered IPr-based complex showed the highest catalytic activity. Copyright

Palladium(II) Complexes with Small N-Heterocyclic Carbene Ligands as Highly Active Catalysts for the Suzuki-Miyaura Cross-Coupling Reaction

Szulmanowicz, Michal S.,Gniewek, Andrzej,Gil, Wojciech,Trzeciak, Anna M.

, p. 1152 - 1160 (2013)

Four new palladium(II) complexes of the type [Pd(NHC)2X2] with N-heterocyclic carbene (NHC) ligands of relatively small steric hindrance were prepared and characterized by using spectroscopic and X-ray methods. For [Pd(bmim-y)2Br2] (bmim-y=1-butyl-3-methylimidazol-2-ylidene), crystals of both cis and trans isomers were obtained. All the studied complexes demonstrated very high activity in Suzuki-Miyaura cross-coupling in ethylene glycol, which yielded turnover numbers of up to 760000. High activity was also observed if NaBPh4 was used instead of PhB(OH)2, and the best results (turnover number=580000) were obtained with [Pd(emim-y)2Cl2] (emim-y=1-ethyl-3-methylimidazol-2-ylidene). In the reaction mixture, different forms containing [Pdx(NHC)y]+ fragments (x=1-4, y=2-5) were identified by using ESI-MS. In the presence of Suzuki-Miyaura reaction substrates, catalytic palladium intermediates with aryl groups-[Pd(NHC)2Ph]+ and [Pd3(NHC)4Ph]+-were detected. Additional mechanistic investigations, such as TEM observations and mercury poisoning experiments, substantiated the formation of nanoparticles as a catalyst resting state. These heterogeneous particles serve as a reservoir for soluble palladium species-atoms or clusters that function as homogeneous catalysts for the Suzuki-Miyaura reaction.

Controlled synthesis of nickel(ii) dihalides bearing two different or identical N-heterocyclic carbene ligands and the influence of carbene ligands on their structures and catalysis

Liu, Zhi-Hong,Xu, Yan-Chao,Xie, Ling-Zhi,Sun, Hong-Mei,Shen, Qi,Zhang, Yong

, p. 4697 - 4706 (2011)

Ni(ii) dihalides bearing two different or identical NHC ligands have been prepared via a controlled indene elimination synthesis, and the former product provides a new route for the design of biscarbene Ni(ii)-based catalysts. The indene elimination reaction of the indenynickel(ii) complex (1-H-Ind)Ni(NHC)X (Ind = indenyl) with one equiv. of a distinct imidazolium salt at 100 °C afforded the first example of Ni(ii) dihalides bearing two different NHC ligands, i.e., Ni(iPr)(IPr)X2 [iPr = 1,3-diisopropylimidazol-2- ylidene, IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene), X = Cl, 1; X = Br, 2] and Ni(iPr)(IMes)Br2 [IMes = 1,3-bis(mesityl)imidazol-2- ylidene, 3]. Alternatively, complexes 1-3 can be synthesized using a bis-indenyl Ni(ii) complex (1-H-Ind)2Ni as starting materials via a step-by-step indene elimination at different reaction temperatures. The direct reaction of (1-R-Ind)2Ni (R = H or Me) with two equiv. of imidazolium salts at 100 °C afforded Ni(ii) dihalides bearing two identical NHC ligands, i.e., Ni(iPr)X2 (X = Cl, 4; X = Br, 5) and Ni(IPr)Cl2 (6). All of these complexes were characterized by elemental analysis, NMR spectroscopy and X-ray crystallography for complexes 1-5. The two identical or different NHC ligands in complexes 1-6 changed the coordination sphere of the nickel center from a typical square-planar geometry to a slightly tetrahedral array. A preliminary catalytic study on the cross-coupling reactions of aryl Grignard reagents with aryl halides revealed that complexes 1 and 2 possess the highest activity. In comparison, complexes 3 and 6 exhibited moderate activity and the least active complexes were 4 and 5.

Highly active Pd nanoparticles dispersed on amine functionalized layered double hydroxide for Suzuki coupling reaction

Singha, Sudarshan,Sahoo, Mitarani,Parida

, p. 7130 - 7132 (2011)

The synthesis of well dispersed palladium nanoparticles (1-5 nm) on diamine functionalized LDH is reported. The heterogeneous catalyst displayed unprecedented activity in Suzuki coupling reaction.

Mechanistic and asymmetric investigations of the Au-catalysed cross-coupling between aryldiazonium salts and arylboronic acids using (P,N) gold complexes

Tabey, Alexis,Berlande, Murielle,Hermange, Philippe,Fouquet, Eric

, p. 12867 - 12870 (2018)

In order to explore the different mechanisms possibly occurring in the Au-catalysed cross-coupling of ArN2BF4 and ArB(OH)2 in the presence of CsF, various stoichiometric experiments were performed on gold complexes with (P,N) ligands. Employing 2-pyridylphenyl-diphenylphosphine allowed us to suggest three different mechanistic pathways, starting either with a transmetallation step, via two consecutive single electron transfers, or by implying a transmetallation between Au(i) and Au(iii) species. Moreover, when using commercially available chiral (P,N) ligands, the asymmetric formation of atropoisomeric biaryls from suitable aryldiazonium salts and arylboronic acids could be achieved with e.e. up to 26%.

N,N-Bis(2-hydroxyethyl)-2-Aminoethanesulfonic Acid-Assisted Liquid-phase Growth of Au@Pd coreshell nanoparticles with high catalytic activity

Zhang, Wei,Zhao, Huiping,Lu, Zhong,Chen, Fengxi,Chen, Rong

, p. 1371 - 1373 (2015)

Au@Pd coreshell nanoparticles were successfully synthesized via sequential reduction of Au(III) and Pd(II) ions with N,N-bis(2-hydroxyethyl)-2-Aminoethanesulfonic acid (BES) at room temperature. Their size and morphology could be changed by varying the BES concentration and pH value of the reaction system. The Au@Pd coreshell nanoparticles exhibited significantly higher catalytic activity for various Suzuki reactions than monometallic Pd or Au nanoparticles. The size-dependent catalytic activity was also observed, i.e., the Au@Pd coreshell nanoparticles of 10nm showed higher activity.

Hemicelluloses supported palladium/xylan nanocomposites containing N and O ligands: Highly-performance heterogeneous catalysts for Suzuki reaction

Du, Fan,Zhang, Lei,Ma, Jiliang,Peng, Xinwen

, p. 224 - 231 (2019)

Two kinds of xylan/palladium catalysts (PACMX-Pd and EDAX-Pd) were simply fabricated by integrating two N bidentate ligands into the skeleton of oxygen-rich xylan and followed with the in-situ reduction of palladium. The Pd loading in PACMX-Pd and EDAX-Pd nanocomposites was 0.353 mmol/g and 0.302 mmol/g, respectively. The catalysts exhibited an excellent catalytic activity for the Suzuki reaction with a yield of high up to 100% as well as a superior turnover frequency (TOF: 9626 h?1). Moreover, the catalysts showed outstanding stability and could be reused for at least 5 times without significant decrease in activity. Compared with other polymers and non-polymers supported palladium catalysts, the as-prepared biomass-based catalysts possess potential applications in a wide range of organic catalysis.

The application of organic bases in microwave-promoted Suzuki coupling reactions in water

Chanthavong, Florine,Leadbeater, Nicholas E.

, p. 1909 - 1912 (2006)

Traditionally, mineral bases are used in Suzuki coupling protocols. The use of DBU or DABCO as alternative bases for the reaction is reported and the application discussed.

Suzuki-Miyaura cross-coupling reaction between aryl halides and phenylboronic acids over gold nano-particles supported on MgO (or CaO) and other metal oxides

Dumbre,Yadav,Bhargava,Choudhary

, p. 134 - 140 (2013)

Gold nano-particles-supported alkaline earth metal oxides, particularly MgO or CaO, show high catalytic activity in the Suzuki-Miyaura cross-coupling reaction in the presence of K2CO3 and DMF (as a solvent). The catalytic activity is strongly influenced by the nature or type of metal oxide support (viz. alkaline earth oxide, Group IIIA metal oxide, transition metal oxide, or rare earth oxide actinide oxide). It is also strongly influenced by the nature of aryl halide (aryl iodide, bromide, chloride, or fluoride), amount of K2CO3 in the reaction mixture and catalyst calcination temperature. Influence of reaction parameters viz. temperature and time and different substituents in aryl halides and/or phenylboronic acids on the biphenyl product yield in the reaction over Au/MgO catalyst has also been investigated. The catalyst showed excellent reusability in the reaction. Moreover, it is ligand-free and also has much lower cost than the commonly used homogeneous and heterogeneous Pd catalysts.

Heterogeneous Suzuki and Stille coupling reactions using highly efficient palladium(0) immobilized MCM-41 catalyst

Jana, Sreyashi,Haldar, Satyajit,Koner, Subratanath

, p. 4820 - 4823 (2009)

An efficient palladium(0) immobilized MCM-41 catalytic system for C-C cross-coupling reaction has been developed. Ligand-free Pd(0)-MCM-41 catalyst can be successfully used in coupling reaction between various aryl halides including deactivated chlorobenzene with aryl borane and organotin to give biaryls in excellent yields with high turnover frequency (TOF) (the maximal TOFs are up to 6990 for the reaction of bromobenzene with phenylboronic acid). The catalyst can be recycled and reused without any loss of catalytic activity.

Synthesis of a recyclable and efficient Pd(ii) 4-(2-pyridyl)-1,2,3-triazole complex over a solid periodic mesoporous organosilica support by "click reactions" for the Stille coupling reaction

Sharma, Priti,Singh

, p. 43070 - 43079 (2014)

A highly efficient, reusable B-PMO-TZ-Pd(ii) catalyst was synthesized by anchoring 4-(2-pyridyl)-4-(2-pyridyl)-1,2,3-triazole ligand over the surface of an organo-functionalized benzene support containing periodic mesoporous organosilica (B-PMO) via "click reaction" and the subsequent complexation with PdCl2. B-PMO materials with uniform hexagonal arrangements were prepared using C16 alkyl trimethyl ammonium bromide [CTAB] surfactant under basic conditions. The physiochemical properties of the functionalised catalyst were analysed by elemental analysis, ICP-OES, XRD, N2 sorption, TGA & DTA, solid state 13C, 29Si NMR spectra, FT-IR, XPS, UV-vis, SEM and TEM. XRD and N2 sorption revealed the morphological and textural properties of the synthesized catalyst, confirming that ordered mesoporous channel structure was retained even after the multistep synthetic procedure. The (100), (110) and (200) reflections in B-PMO are evidence of its good structural stability and the existence of long range order. The TGA-DTA results reveal that the synthesized catalyst B-PMO-TZ-Pd(ii) was thermally stable, even at high temperature. The organic moieties anchored over the surface of B-PMO were demonstrated by solid state 13C NMR and FT-IR spectroscopy. Solid state 29Si NMR spectroscopy provides information about the degree of functionalization of the surface silanol group. The electronic environment and oxidation state of Pd in B-PMO-TZ-Pd(ii) were monitored by XPS and UV-visible techniques. Moreover, the morphologies and topographic information of the synthesized B-PMO-TZ-Pd(ii) catalyst were confirmed by SEM and TEM analyses. The catalytic properties of the catalyst for the Stille coupling reaction were screened, and higher catalytic activities with high TONs were observed. The anchored solid B-PMO-TZ-Pd(ii) catalyst can be recycled efficiently and reused several (four) times without a major loss in reactivity. This journal is

Transition-metal-free Suzuki-type coupling reactions: Scope and limitations of the methodology

Leadbeater, Nicholas E.,Marco, Maria

, p. 5660 - 5667 (2003)

The scope and limitations of the transition-metal-free Suzuki-type coupling of aryl halides and arylboronic acids to form biaryls are presented. Confirmation that the reaction is indeed metal-free is presented. The effects of changing base, solvent, reaction temperature, phase-transfer catalyst, and substrate are shown and the implications of these results discussed in terms of their impact on the synthetic versatility of the methodology. The main findings are that the reaction works well for aryl bromides, water is necessary as a solvent for the reaction, the optimum temperature for the reaction is 150 °C, the reaction is best performed by using microwave promotion with the exception of an electron-poor aryl bromide example where conventional heating may be used, only limited boronic acids can be used as coupling partners, sodium carbonate is the best base for the reaction, tetrabutylammonium bromide proves to be the best phase-transfer catalyst for the reaction, the reaction is limited to couplings between aryl halides and aryl boronic acids with sp2-sp3 couplings proving ineffective, and NaBPh4 can be used in the place of phenylboronic acid as a phenylating agent.

Three-coordinate nickel(i) complexes stabilised by six-, seven- and eight-membered ring N-heterocyclic carbenes: Synthesis, EPR/DFT studies and catalytic activity

Page, Michael J.,Lu, Wei Y.,Poulten, Rebecca C.,Carter, Emma,Algarra, Andres G.,Kariuki, Benson M.,MacGregor, Stuart A.,Mahon, Mary F.,Cavell, Kingsley J.,Murphy, Damien M.,Whittlesey, Michael K.

, p. 2158 - 2167 (2013)

Comproportionation of [Ni(cod)2] (cod=cyclooctadiene) and [Ni(PPh3)2X2] (X=Br, Cl) in the presence of six-, seven- and eight-membered ring N-aryl-substituted heterocyclic carbenes (NHCs) provides a route to a series of isostructural three-coordinate Ni I complexes [Ni(NHC)(PPh3)X] (X=Br, Cl; NHC=6-Mes 1, 6-Anis 2, 6-AnisMes 3, 7-o-Tol 4, 8-Mes 5, 8-o-Tol 6, O-8-o-Tol 7). Continuous wave (CW) and pulsed EPR measurements on 1, 4, 5, 6 and 7 reveal that the spin Hamiltonian parameters are particularly sensitive to changes in NHC ring size, N substituents and halide. In combination with DFT calculations, a mixed SOMO of |3dz2〉 and |3dx2 - y2〉 character, which was found to be dependent on the complex geometry, was observed and this was compared to the experimental g values obtained from the EPR spectra. A pronounced 31P superhyperfine coupling to the PPh3 group was also identified, consistent with the large spin density on the phosphorus, along with partially resolved bromine couplings. The use of 1, 4, 5 and 6 as pre-catalysts for the Kumada coupling of aryl chlorides and fluorides with ArMgY (Ar=Ph, Mes) showed the highest activity for the smaller ring systems and/or smaller substituents (i.e., 1>4≈6?5). Copyright

Suzuki-Miyaura reaction catalyzed by a dendritic phosphine-palladium complex

Fujita, Ken-Ichi,Hattori, Hatsuhiko

, p. 1485 - 1492 (2016)

We prepared several of a new type of a dendritic ligand with a phosphine core by using tris(4-hydroxyphenyl)phosphine oxide and poly(aryl ether) dendron. In particular, when an amphiphilic dendritic phosphine-palladium complex was used as a catalyst, the aqueous media Suzuki-Miyaura reaction proceeded smoothly to provide the corresponding cross-coupling product at 50 °C. A positive dendritic effect on chemical yields was observed.

Disubstituted benzenes from acyclic precursors by a [5+1] annulation

Daniels, David S. B.,Brown, John M.,Gayral, Maud,Xu, Yingjian,Stewart, Malcolm I.

, p. 1387 - 1390 (2009)

Horner-Wadsworth-Emmons reaction of stannylvinylphosphonates with aldehydes and mild thermal cyclisation provides disubstituted arylstannanes. Subsequent Stille coupling leads to regiospecific synthesis of m- and p-terphenyls. Georg Thieme Verlag Stuttgar

Palladium-catalysed Grignard cross-coupling using highly concentrated Grignards in methyl-tetrahydrofuran

Milton, Edward J.,Clarke, Matthew L.

, p. 381 - 383 (2010)

The cross-coupling of Grignard reagents at 5 molar concentration in methyl-tetrahydrofuran with no added reaction solvents can be achieved with the appropriate matching of catalyst to substrate, significantly reducing solvent use when compared to a typical protocol in tetrahydrofuran. Me-THF was also used in an improved microwave accelerated synthesis of the [Pd(L)Cl2] pre-catalysts from sodium tetrachloropalladate in very high yield.

Combining N-heterocyclic carbenes and phosphines: Improved palladium(II) catalysts for aryl coupling reactions

Weskamp, Thomas,Boehm, Volker P.W.,Herrmann, Wolfgang A.

, p. 348 - 352 (1999)

Complexes of the type (NHC)Pd(PR3)I2 with bulky N-heterocyclic carbenes (NHC) are efficient catalysts for aryl coupling reactions such as the Suzuki and Stille cross-coupling reaction. These catalysts combine the advantageous stability of bis(carbene) complexes and the good activity of the bis(phosphine) complexes in these reactions. Both arylbromides and arylchlorides can be used as substrates.

A highly controllable, effective, and recyclable magnetic-nanoparticle-supported palladium catalyst for the Suzuki–Miyaura cross-coupling reaction

Ye, Lu,Liu, Xiaojing,Lu, Yangcheng

, p. 36 - 43 (2021)

In this work, a highly efficient palladium catalyst was facilely immobilized on the surfaces of magnetic nanoparticles with the coordination of N-heterocyclic carbene. The prepared Pd–NHC@NCPs were characterized by transmission electron microscopy, Fourier transform infrared spectroscopy, energy dispersive spectroscopy, X-ray photoelectron spectroscopy, and inductively coupled plasma atomic emission spectrometry. With suitably designed emulsion polymerization and immobilization, the final palladium loading could reach 0.78 mmol/g. The catalyst showed outstanding catalytic performance in the Suzuki–Miyaura cross-coupling reaction among various substrates, with little catalyst usage (0.03 mol.%), short reaction time, and mild reaction conditions. In addition, the catalyst could be separated conveniently from the reacting system with an external magnet and show good catalytic performance even after being reused five times or more, indicating good recyclability.

Fluorine-substituted arylphosphine for an NHC-Ni(I) system, air-stable in a solid state but catalytically active in solution

Matsubara, Kouki,Fujii, Takahiro,Hosokawa, Rion,Inatomi, Takahiro,Yamada, Yuji,Koga, Yuji

, (2019)

Monovalent NHC-nickel complexes bearing triarylphosphine, in which fluorine is incorporated onto the aryl groups, have been synthesized. Tris(3,5-di(trifluoromethyl)phenyl)phosphine efficiently gave a monovalent nickel bromide complex, whose structure was determined by X-ray diffraction analysis for the first time. In the solid state, the Ni(I) complex was less susceptible to oxidation in air than the triphenylphosphine complex, indicating greatly improved solid-state stability. In contrast, the Ni(I) complex in solution can easily liberate the phosphine, high catalytic activity toward the Kumada–Tamao–Corriu coupling of aryl bromides.

Fe3O4 nanoparticles-supported palladium-bipyridine complex: Effective catalyst for suzuki coupling reaction

Zhang, Yan-Qi,Wei, Xian-Wen,Yu, Rui

, p. 256 - 262 (2010)

Fe3O4 nanoparticles-supported palladium-2, 2-bipyridine complex was synthesized and used as catalyst for Suzuki coupling reactions between different aryl iodides and bromides with phenyl boronic acid under mild conditions. This catalyst can be separated magnetically. However, due to the aggregation of catalyst with the increase in reaction times, the activity dropped dramatically from >99% for the first time use to 45% for the fourth time use and then kept constant subsequently.

Palladium Immobilized on a Polyimide Covalent Organic Framework: An Efficient and Recyclable Heterogeneous Catalyst for the Suzuki–Miyaura Coupling Reaction and Nitroarene Reduction in Water

Dong, Zhenhua,Pan, Hongguo,Gao, Pengwei,Xiao, Yongmei,Fan, Lulu,Chen, Jing,Wang, Wentao

, p. 299 - 306 (2021/05/10)

An efficient and recyclable Pd nano-catalyst was developed via immobilization of Pd nanoparticles on polyimide linked covalent organic frameworks (PCOFs) that was facilely prepared through condensation of melamine and 3,3′,4,4′-biphenyltetracarboxylic dianhydride. The Pd nanoparticles (Pd NPs) catalyst was thoroughly characterized by FT-IR, XRD, SEM, TEM. Furthermore, the catalytic activity of Pd NPs catalyst was evaluated by Suzuki–Miyaura coupling reaction and nitroarene reduction in water, respectively. The excellent yields of corresponding products revealing revealed that the Pd NPs catalyst could be applied as an efficient and reusable heterogeneous catalyst for above two reactions. Graphical Abstract: [Figure not available: see fulltext.]

An Imidazole-Rich Pd(II)-Polymer Pre-catalyst for the Suzuki-Miyaura Coupling: Stability Influenced by Dissolved Oxygen and Reactants Concentration

Nishida, Elvis N.,Leopoldino, Elder C.,Zaramello, Laíze,Centurion, Higor A.,Gon?alves, Renato V.,Affeldt, Ricardo F.,Campos, Carlos E. M.,Souza, Bruno S.

, (2022/02/01)

Herein a novel Pd(II)-polymeric pre-catalyst was prepared by coordinating Pd(II) ions to a low cost imidazole/carboxylate-rich polymer. The material displays good activity in the Suzuki-Miyaura coupling towards a range of aryl bromides and iodides in iPrOH/H2O mixtures at 25 or 60 °C. Catalyst longevity and recyclability proved to be sensitive to the concentration of the cross-coupling partners. When the concentration of PhBr is high ([PhBr]=250 mmol L?1), inactive Pd(0) aggregates were detected. On the other hand, when the reaction was performed at 20-fold dilution ([PhBr]=12.5 mmol L?1) the material could be reused up to 12 times without significant loss of catalytic activity. In this condition, minimum amount of Pd(0) was detected by XPS analysis and no Pd(0) aggregates were observed by XRPD. Importantly, it was found that the presence of oxygen is fundamental for avoiding formation of inactive Pd(0) aggregates.

Organocatalytic synthesis of (Het)biaryl scaffoldsviaphotoinduced intra/intermolecular C(sp2)-H arylation by 2-pyridone derivatives

Das, Tapas Kumar,Kundu, Mrinalkanti,Mondal, Biswajit,Ghosh, Prasanjit,Das, Sajal

, p. 208 - 218 (2021/12/29)

A uniqueN,O-bidentate ligand 6-oxo-1,6-dihydro-pyridone-2-carboxylic acid dimethylamide (L1) catalyzed direct C(sp2)-H (intra/intermolecular) arylation of unactivated arenes has been developed to expedite access to (Het)biaryl scaffolds under UV-irradiation at room temperature. The protocol tolerated diverse functional groups and substitution patterns, affording the target products in moderate to excellent yields. Mechanistic investigations were also carried out to better understand the reaction pathway. Furthermore, the synthetic applicability of this unified approach has been showcasedviathe construction of biologically relevant 4-quinolone, tricyclic lactam and sultam derivatives.

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