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Search for "triazine" in Full Text gives 67 result(s) in Beilstein Journal of Organic Chemistry.

(E,Z)-1,1,1,4,4,4-Hexafluorobut-2-enes: hydrofluoroolefins halogenation/dehydrohalogenation cascade to reach new fluorinated allene

  • Nataliia V. Kirij,
  • Andrey A. Filatov,
  • Yurii L. Yagupolskii,
  • Sheng Peng and
  • Lee Sprague

Beilstein J. Org. Chem. 2024, 20, 452–459, doi:10.3762/bjoc.20.40

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  • demonstrated that 1,1,1,4,4,4-hexafluorobut-2-ene reacts with dithietane, sulfur and KF with the formation of the corresponding 1,3-dithiole [16]. Also, a recent patent presents a method for the preparation of 5,6-bis(trifluoromethyl)-1,2,4-triazine-3-carboxylic acid ethyl ester starting from 1,1,1,4,4,4
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Published 27 Feb 2024

Trifluoromethylated hydrazones and acylhydrazones as potent nitrogen-containing fluorinated building blocks

  • Zhang Dongxu

Beilstein J. Org. Chem. 2023, 19, 1741–1754, doi:10.3762/bjoc.19.127

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  • ] (Scheme 12a). Meanwhile, the Jasiński group turned their attention to the [3 + 3] cycloaddition of α-amino esters and trifluoromethylated hydrazonoyl halides and demonstrated the efficient synthesis of trifluoromethylated 1,2,4-triazine derivatives [80] (Scheme 12b). Difluoromethylated compounds play an
  • trifluoromethylated hydrazonoyl halides. [3 + 2]/[3 + 3] Cycloadditions of trifluoromethylated hydrazonoyl halides. Substrate scope for [3 + 2] cycloadditions with trifluoroacetonitrile imines reported by Jasiński’s team and other groups. Synthesis of trifluoromethylated 1,2,4-triazole and 1,2,4-triazine derivatives
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Published 15 Nov 2023

Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines via a base-induced rearrangement of functionalized imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazines

  • Dmitry B. Vinogradov,
  • Alexei N. Izmest’ev,
  • Angelina N. Kravchenko,
  • Yuri A. Strelenko and
  • Galina A. Gazieva

Beilstein J. Org. Chem. 2023, 19, 1047–1054, doi:10.3762/bjoc.19.80

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  • esters are also suitable substrates for the reaction. In this case hydrolysis and thiazole ring expansion were accompanied with the change of the thiazolotriazine junction type from thiazolo[3,2-b][1,2,4]triazine to thiazino[2,3-c][1,2,4]triazine. Keywords: N,S-heterocycles; ring expansion; skeletal
  • closely related hybrid compounds including fragments of 1,3-thiazine and imidazo-1,2,4-triazine is still highly relevant. Earlier we have demonstrated that imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazines and their derivatives functionalized at position 6 are capable of undergoing skeletal rearrangements and
  • derivatives undergo rearrangement into the corresponding isomeric derivatives of imidazo[4,5-e]thiazolo[2,3-c]-1,2,4-triazine [18][21] (Scheme 1A). In the present study, we report a new base-induced recyclization of functionalized imidazothiazolotriazines 1 and 2 resulting in derivatives of the new
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Published 28 Jul 2023

Mechanochemical bottom-up synthesis of phosphorus-linked, heptazine-based carbon nitrides using sodium phosphide

  • Blaine G. Fiss,
  • Georgia Douglas,
  • Michael Ferguson,
  • Jorge Becerra,
  • Jesus Valdez,
  • Trong-On Do,
  • Tomislav Friščić and
  • Audrey Moores

Beilstein J. Org. Chem. 2022, 18, 1203–1209, doi:10.3762/bjoc.18.125

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  • such techniques are beneficial not only from a green chemistry perspective [11], but they also afford conditions conducive to new reactivities and the development of novel materials [9]. Previously, we have explored the synthesis of phosphorus-bridged g-CN-type materials produced from a triazine unit
  • and found that the resulting material featured good photochemical properties (Scheme 1) [38]. Yet, conventional g-CN materials are not based on triazine units, but rather on heptazine ones, thus featuring more open structures. In an effort to replicate a structure closer to known g-CN systems, we
  • -based materials showed similar resonances to previous work by our group on phosphorus-linked triazine networks [38]. The 31P MAS NMR of g-h-PCN showed a broad resonance centered around −8.9 ppm, with a sharp residual phosphate resonance at 0.9 ppm (Figure 3a). NMR analysis of similar materials, by our
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Published 12 Sep 2022

Synthesis, optical and electrochemical properties of (D–π)2-type and (D–π)2Ph-type fluorescent dyes

  • Kosuke Takemura,
  • Kazuki Ohira,
  • Taiki Higashino,
  • Keiichi Imato and
  • Yousuke Ooyama

Beilstein J. Org. Chem. 2022, 18, 1047–1054, doi:10.3762/bjoc.18.106

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  • -based photoabsorption and fluorescence bands of OTK-2 appear in a shorter wavelength region than those of the corresponding (D–π)2A-type fluorescent dye having an azine ring (pyridine, pyrazine or triazine ring) as a substitute for the phenyl ring. However, the molar extinction coefficient (εmax) and
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Published 18 Aug 2022

Substituent effect on TADF properties of 2-modified 4,6-bis(3,6-di-tert-butyl-9-carbazolyl)-5-methylpyrimidines

  • Irina Fiodorova,
  • Tomas Serevičius,
  • Rokas Skaisgiris,
  • Saulius Juršėnas and
  • Sigitas Tumkevicius

Beilstein J. Org. Chem. 2022, 18, 497–507, doi:10.3762/bjoc.18.52

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  • such as triazine, diazines or aromatics containing cyano and sulfone groups are popular acceptor units for the construction of highly efficient TADF emitters [8][9][10][11]. Pyrimidine (1,3-diazine) owing to its aromaticity, significant π-deficiency, strong electron affinity, high luminous efficiency
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Published 05 May 2022

Site-selective reactions mediated by molecular containers

  • Rui Wang and
  • Yang Yu

Beilstein J. Org. Chem. 2022, 18, 309–324, doi:10.3762/bjoc.18.35

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  • accommodated in the cavity of A through π–π stacking interactions between the naphthalene ring of 3 and a triazine ligand of A from the X-ray crystallographic analysis. In the control experiment, without host A, only 44% yield of the conventional 9,10-adduct 4 was produced without any 1,4-adduct product
  • reaction, the anthracene moiety stacks onto the planar triazine of B through π–π stacking and possible charge-transfer interaction between each other, which stabilizes the complex. However, after the reaction, the framework of the product is bent at the 9,10-position, which undermines the host–guest
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Published 14 Mar 2022

Study on the interactions between melamine-cored Schiff bases with cucurbit[n]urils of different sizes and its application in detecting silver ions

  • Jun-Xian Gou,
  • Yang Luo,
  • Xi-Nan Yang,
  • Wei Zhang,
  • Ji-Hong Lu,
  • Zhu Tao and
  • Xin Xiao

Beilstein J. Org. Chem. 2021, 17, 2950–2958, doi:10.3762/bjoc.17.204

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  • to yield different metal-organic frameworks [6][7][8][9][10][11], but also can be used as analytical reagents for the detection of different organic and inorganic substances [12][13][14]. Among the various central molecules for the synthesis of Schiff bases, melamine (2,4,6-triamino-s-triazine) has
  • electropositivity can be a perfect candidate for the study of outer-surface interaction of cucurbit[n]urils [21][22][23][24]. In this work, nitrogen-rich melamine is used as the center molecule to synthesize the Schiff base 2,4,6-tris(((4-(4-carboxybutyl)phenyl)methylene)amino)-1,3,5-triazine (TBT) through the
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Published 17 Dec 2021

Effect of a twin-emitter design strategy on a previously reported thermally activated delayed fluorescence organic light-emitting diode

  • Ettore Crovini,
  • Zhen Zhang,
  • Yu Kusakabe,
  • Yongxia Ren,
  • Yoshimasa Wada,
  • Bilal A. Naqvi,
  • Prakhar Sahay,
  • Tomas Matulaitis,
  • Stefan Diesing,
  • Ifor D. W. Samuel,
  • Wolfgang Brütting,
  • Katsuaki Suzuki,
  • Hironori Kaji,
  • Stefan Bräse and
  • Eli Zysman-Colman

Beilstein J. Org. Chem. 2021, 17, 2894–2905, doi:10.3762/bjoc.17.197

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  • %, with Commission Internationale de l’Éclairage coordinate of (0.22, 0.47), at 1 mA cm−2. Keywords: blue emitters; dimer; indolocarbazole; orientation; outcoupling effect; solution-processed OLEDs; TADF emitters; triazine; Introduction Organic thermally activated delayed fluorescence (TADF) materials
  • eV for DICzTRZ vs −1.75 eV for ICzTRZ) since the electronic environment surrounding the t-Bu-triazine remains essentially unperturbed (Figure 3). Optoelectronic properties The electrochemical properties of the two materials were studied in degassed DCM with tetra-n-butylammonium hexafluorophosphate
  • transitions was also evaluated by analysis of the natural transition orbitals (NTOs) (see Supporting Information File 1, Table S2). The T1 and T2 HONTO and LUNTO (highest occupied and lowest unoccupied natural Transition orbitals) are localized on the central diindolocarbazole and adjacent triazine
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Published 08 Dec 2021

Iron-catalyzed domino coupling reactions of π-systems

  • Austin Pounder and
  • William Tam

Beilstein J. Org. Chem. 2021, 17, 2848–2893, doi:10.3762/bjoc.17.196

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Published 07 Dec 2021

Synthesis of new pyrazolo[1,2,3]triazines by cyclative cleavage of pyrazolyltriazenes

  • Nicolai Wippert,
  • Martin Nieger,
  • Claudine Herlan,
  • Nicole Jung and
  • Stefan Bräse

Beilstein J. Org. Chem. 2021, 17, 2773–2780, doi:10.3762/bjoc.17.187

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  • [3,4-d][1,2,3]triazine core with commercially available building blocks, enabling the extension of the protocol to gain other derivatives straightforwardly. Attempts to synthesize 3,7-substituted-4,7-dihydro-3H-pyrazolo[3,4-d][1,2,3]triazines, the regioisomers of the successfully gained 3,6-substituted
  • -methylamide-substituted aryltriazenes 7 could be efficiently converted into 3,4-dihydrobenzo[d][1,2,3]triazine derivatives 8 [37] (Scheme 2). In this context, triazenes have shown beneficial properties as they can be used as protected diazonium species which can be handled and converted in various
  • transformations without decomposition [37][38][39]. In the herein presented study, we apply the cyclative cleavage reaction to pyrazolyltriazenes instead of aryltriazenes, which results in the synthesis of diverse pyrazolo[3,4-d][1,2,3]-3H-triazine derivatives 5. Results and Discussion According to the literature
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Published 22 Nov 2021

Photoinduced post-modification of graphitic carbon nitride-embedded hydrogels: synthesis of 'hydrophobic hydrogels' and pore substructuring

  • Cansu Esen and
  • Baris Kumru

Beilstein J. Org. Chem. 2021, 17, 1323–1334, doi:10.3762/bjoc.17.92

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  • -sustainable semiconductors are slowly being replaced by a new generation of semiconductors. Graphitic carbon nitride (g-CN) is a metal-free polymeric semiconductor that is mainly composed of carbon and nitrogen elements by tri-s-triazine, triazine imide, or heptazine repeating units [16][17][18]. g-CN
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Published 21 May 2021

Synthesis of functionalized imidazo[4,5-e]thiazolo[3,2-b]triazines by condensation of imidazo[4,5-e]triazinethiones with DMAD or DEAD and rearrangement to imidazo[4,5-e]thiazolo[2,3-c]triazines

  • Alexei N. Izmest’ev,
  • Dmitry B. Vinogradov,
  • Natalya G. Kolotyrkina,
  • Angelina N. Kravchenko and
  • Galina A. Gazieva

Beilstein J. Org. Chem. 2021, 17, 1141–1148, doi:10.3762/bjoc.17.87

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  • -triazine-3-thiones with acetylenedicarboxylic acid dimethyl and diethyl esters (DMAD and DEAD) and subsequent base-catalyzed rearrangement of the obtained imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazines into regioisomeric imidazo[4,5-e]thiazolo[2,3-c]-1,2,4-triazine derivatives. Keywords: amidine
  • rearrangement; cyclocondensation; heterocycles; thiazolidine-4-one; 1,2,4-triazine; Introduction The thiazolidin-4-one heterocyclic system is a well-known, accessible and, as a consequence, a widely used pharmacophore in the chemistry of biologically active compounds possessing antimicrobial [1
  • only products, namely, thiazolo[3,2-b]-1,2,4-triazines 2 (Scheme 1) while the regioisomeric thiazolo[2,3-с]-1,2,4-triazine derivatives remain unavailable. The present work is devoted to the development of methods for the regiodirected synthesis of two series of functionalized imidazothiazolotriazines
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Published 14 May 2021

Synthetic accesses to biguanide compounds

  • Oleksandr Grytsai,
  • Cyril Ronco and
  • Rachid Benhida

Beilstein J. Org. Chem. 2021, 17, 1001–1040, doi:10.3762/bjoc.17.82

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  • production of biodiesel [5][80], intermediates for triazine synthesis [48], etc. Some derivatives were grafted onto polystyrene resins for catalytic uses [5]. Various solvents and temperatures were used such as hot DMF [5], neat [79], toluene or hexane at 25–100 °C [79]. Generally, higher temperatures seem
  • equivalents of the carbodiimide in the reaction with N,N’-disubstituted guanidines resulted in the formation of 1,2-dihydro-1,3,5-triazine derivatives as the main products of the cycloaddition reaction [82]. They also showed that increasing the amount of the carbodiimide to 3 equivalents led to excellent
  • triazine yields in refluxing THF (Scheme 42). The mechanism of this reaction proceeds via the formation of a nonisolated triguanide intermediate, that spontaneously cyclizes to the 1,3,5-triazine derivative after elimination of the amine counterpart (Scheme 43). The authors proposed two plausible
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Published 05 May 2021

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

  • Shivani Gulati,
  • Stephy Elza John and
  • Nagula Shankaraiah

Beilstein J. Org. Chem. 2021, 17, 819–865, doi:10.3762/bjoc.17.71

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  • 115, could be only obtained. The regioisomer A being less stable due to steric hindrance between the amino and the aryl group rearranges to give desired product 115. The mechanism involved in the formation of intermediate B is similar to the mechanism proposed for amino-1,3,5-triazine ring
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Published 19 Apr 2021

Synthetic reactions driven by electron-donor–acceptor (EDA) complexes

  • Zhonglie Yang,
  • Yutong Liu,
  • Kun Cao,
  • Xiaobin Zhang,
  • Hezhong Jiang and
  • Jiahong Li

Beilstein J. Org. Chem. 2021, 17, 771–799, doi:10.3762/bjoc.17.67

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  • in good to excellent yield. The protocol conforms to the characteristics of green and environmental conservation, having a reaction time of only 1 hour, achieving the purpose of saving energy. In 2019, Liang and colleagues [24] reported a method for preparing perfluoroalkyl-s-triazine via visible
  • -light-promoted [5 + 1] cyclization initiated by an EDA complex. Perfluoroalkyl-s-triazine derivative 45 was synthesized by the reaction of biguanidine derivative 44 and perfluoroalkyl iodide 28 in the presence of sodium hydroxide (Scheme 15). Considering that oxygen played an indispensable role in the
  • process, the authors supposed that it may facilitate single-electron transfer between biguanidine anion and perfluoroalkyl halide. By constructing two C–N bonds at the same time, the triazine heterocyclic structure that is commonly utilized in medical and material fields was accomplished by [5 + 1
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Published 06 Apr 2021
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  • explore their potential computationally within TADF emitter design. We cross-compare their optoelectronic properties with analog materials using well-studied conjugated electron-withdrawing groups (cyano, benzophenone, and triazine). We investigated two families of structures. The first family consists of
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Published 21 Jan 2021

Optical detection of di- and triphosphate anions with mixed monolayer-protected gold nanoparticles containing zinc(II)–dipicolylamine complexes

  • Lena Reinke,
  • Julia Bartl,
  • Marcus Koch and
  • Stefan Kubik

Beilstein J. Org. Chem. 2020, 16, 2687–2700, doi:10.3762/bjoc.16.219

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  • spectrum at 528 nm (Figure S1 in Supporting Information File 1). Further structural information was obtained by releasing the ligand molecules from the surface of NPrac-1 with iodine, adding a known amount of 2,4,6-trimethoxy-1,3,5-triazine to the solution as an internal standard, and recording an 1H NMR
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Published 02 Nov 2020

Selective and reversible 1,3-dipolar cycloaddition of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with 1,3-diphenylprop-2-en-1-ones under microwave irradiation

  • Alexander P. Molchanov,
  • Mariia M. Efremova,
  • Mariya A. Kryukova and
  • Mikhail A. Kuznetsov

Beilstein J. Org. Chem. 2020, 16, 2679–2686, doi:10.3762/bjoc.16.218

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  • that the Lewis acid-catalyzed reaction of diaziridines with donor–acceptor cyclopropanes and aziridines affords the perhydropyridazine or triazine derivatives, respectively, in good yields [31][32][33]. The use of microwave irradiation in organic synthesis complies with the principles of green
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Published 30 Oct 2020

Microwave-assisted efficient one-pot synthesis of N2-(tetrazol-5-yl)-6-aryl/heteroaryl-5,6-dihydro-1,3,5-triazine-2,4-diamines

  • Moustafa Sherief Moustafa,
  • Ramadan Ahmed Mekheimer,
  • Saleh Mohammed Al-Mousawi,
  • Mohamed Abd-Elmonem,
  • Hesham El-Zorba,
  • Afaf Mohamed Abdel Hameed,
  • Tahany Mahmoud Mohamed and
  • Kamal Usef Sadek

Beilstein J. Org. Chem. 2020, 16, 1706–1712, doi:10.3762/bjoc.16.142

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  • Chemistry, Faculty of Science, Minia University, Minia 61519, Egypt Department of Pharmacology, Faculty of Veterinary Medicine, Cairo University, Giza 12211, Egypt 10.3762/bjoc.16.142 Abstract An efficient one-pot synthesis of N2-(tetrazol-5-yl)-6-aryl/heteroaryl-1,3,5-triazine-2,4-diamine derivatives was
  • developed by reacting 5-amino-1,2,3,4-tetrazole with aromatic aldehydes and cyanamide in pyridine under controlled microwave heating with high yields. X-ray crystallography confirmed the structure of the obtained products. Keywords: microwave irradiation; N2-(tetrazol-5-yl)-6-aryl/heteroaryl-1,3,5-triazine
  • [2], antitumor [3], anti-HIV [4], inhibitor of Trypanosoma brucei [5], angiogenesis inhibitor [6], antiplasmodial antifolates [7], and antimicrobial [8]. Moreover, and in particular N2,6-disubstituted-1,3,5-triazine-2,4-diamines possess a wide range of chemotherapeutic activities [8][9][10][11
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Published 16 Jul 2020

Heterogeneous photocatalysis in flow chemical reactors

  • Christopher G. Thomson,
  • Ai-Lan Lee and
  • Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125

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Published 26 Jun 2020

One-pot synthesis of 1,3,5-triazine-2,4-dithione derivatives via three-component reactions

  • Gui-Feng Kang and
  • Gang Zhang

Beilstein J. Org. Chem. 2020, 16, 1447–1455, doi:10.3762/bjoc.16.120

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  • 100050, China 10.3762/bjoc.16.120 Abstract A catalyst-free one-pot synthetic methodology was developed for the preparation of 1,3,5-triazine-2,4-dithione derivatives through three-component reactions of arylaldehydes, thiourea, and orthoformates. The procedure tolerated a diverse range of arylaldehydes
  • and orthoformates and provided a rapid entry to a variety of 4-aryl-6-(alkylthio)-3,4-dihydro-1,3,5-triazine-2(1H)-thiones (29 examples). The synthetic strategy relies on the dual role of thiourea in the cyclization with the aldehydes and the alkylation via an intermediate imidate formation. The
  • structures of 1,3,5-triazine-2,4-dithione derivatives were characterized by spectroscopic techniques as well as by single crystal X-ray diffraction. Keywords: aldehydes; multicomponent reactions; nitrogen heterocycles; thiourea; triazinethiones; Introduction The construction of nitrogen-containing
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Published 24 Jun 2020

Synthesis and properties of quinazoline-based versatile exciplex-forming compounds

  • Rasa Keruckiene,
  • Simona Vekteryte,
  • Ervinas Urbonas,
  • Matas Guzauskas,
  • Eigirdas Skuodis,
  • Dmytro Volyniuk and
  • Juozas V. Grazulevicius

Beilstein J. Org. Chem. 2020, 16, 1142–1153, doi:10.3762/bjoc.16.101

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  • of the derivatives were in the range of 5.22–5.87 eV. The 3,6-di-tert-butylcarbazole-substituted quinazoline-based compound forms a sky-blue emitting exciplex in solid mixture with the acceptor 2,4,6-tris[3-(diphenylphosphinyl)phenyl]-1,3,5-triazine as well as an orange emitting exciplex with the
  • regarded as a promising candidate for blue exciplex formation in the solid state. Indeed, compound 1 formed a sky-blue emitting exciplex (501 nm) in a solid mixture with the acceptor 2,4,6-tris[3-(diphenylphosphinyl)phenyl]-1,3,5-triazine (PO-T2T). Moreover, an orange exciplex emission with a PL spectrum
  • be in the range of 5.22–5.87 eV. The 3,6-di-tert-butylcarbazole-substituted quinazoline derivative formed a sky-blue emitting exciplex with the acceptor 2,4,6-tris[3-(diphenylphosphinyl)phenyl]-1,3,5-triazine as well as an orange emitting exciplex with the donor 4,4′,4″-tris[3-methylphenyl(phenyl
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Published 28 May 2020

Photophysics and photochemistry of NIR absorbers derived from cyanines: key to new technologies based on chemistry 4.0

  • Bernd Strehmel,
  • Christian Schmitz,
  • Ceren Kütahya,
  • Yulian Pang,
  • Anke Drewitz and
  • Heinz Mustroph

Beilstein J. Org. Chem. 2020, 16, 415–444, doi:10.3762/bjoc.16.40

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  • = −0.64 V [5][84]) or the triazine 89 (Ered = −0.77 V [5]) carrying no charge as acceptor (Scheme 5). Thus, the positive charge of the iodonium cation is likely not the reason because 89 exhibits no charge. Both possess similar reduction potentials but the efficiency to initiate radical polymerization was
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Published 18 Mar 2020

Architecture and synthesis of P,N-heterocyclic phosphine ligands

  • Wisdom A. Munzeiwa,
  • Bernard Omondi and
  • Vincent O. Nyamori

Beilstein J. Org. Chem. 2020, 16, 362–383, doi:10.3762/bjoc.16.35

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  • nucleophiles compared to organometallic or metal phosphides generated through metalation processes. Hayashi et al. [66] used tris(trimethylsilyl)phosphine to control the nucleophilic substitution in the preparation of P,N-(phosphino)triazine ligands (Scheme 5). It was shown that the use of other nucleophiles
  • and/or alkoxy derivatives 29–31. Selectively varying the molar ratio of the silylphosphine nucleophile and the starting reagent 25 resulted in the corresponding bis- and tris(diphenylphosphine)triazine motifs 27 and 28. A subsequent nucleophilic substitution reaction of 27 gave compounds 32 and 33
  • of pyridylphosphine ligands. Synthesis of piperidyl- and oxazinylphosphine ligands. Synthesis of linear multi-chelate pyridylphosphine ligands. Synthesis of chiral acetal pyridylphosphine ligands. Synthesis of diphenylphosphine-substituted triazine ligands. Synthesis of (pyridine-2-ylmethyl)phosphine
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Published 12 Mar 2020
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