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Search for "triphenylphosphine" in Full Text gives 232 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

C3-Alkylation of furfural derivatives by continuous flow homogeneous catalysis

  • Grédy Kiala Kinkutu,
  • Catherine Louis,
  • Myriam Roy,
  • Juliette Blanchard and
  • Julie Oble

Beilstein J. Org. Chem. 2023, 19, 582–592, doi:10.3762/bjoc.19.43

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  • (triethoxysilyl)ethyl)phosphine L1 or triphenylphosphine [40][41][42]. Their synthesis, well-described in the literature, is detailed in Supporting Information File 1 (pp. S3–S6). Moreover, a kinetic study carried out in batch in the presence of the [Ru3(CO)11(L1)] (comp1), [Ru3(CO)10(L1)2] (comp2) or [Ru3(CO)9
  • steps, and thus to consider the direct functionalization of furfural via the in-situ formation of furfurylimine. Furthermore, as the [Ru3(CO)11(PPh3)] comp4 catalyst showed an activity and a solubility in batch similar to comp1, we continued the optimization with the latter, triphenylphosphine being
  • relevant building blocks on a large scale. Experimental Triphenylphosphine triruthenium undecacarbonyl (comp4) Following a slightly modified procedure compared to the one reported [41], triruthenium dodecacarbonyl (1.4 g, 2.19 mmol, 1 equiv) was dissolved in freshly distilled and degassed THF (0.036 M) at
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Published 03 May 2023

Combretastatins D series and analogues: from isolation, synthetic challenges and biological activities

  • Jorge de Lima Neto and
  • Paulo Henrique Menezes

Beilstein J. Org. Chem. 2023, 19, 399–427, doi:10.3762/bjoc.19.31

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  • formation of seco-acid 36. Macrolactonization attempts conducted under high dilution, including the Mitsunobu conditions [35] gave only the cyclic diolide. However, the use of higher dilution conditions and the dropwise addition of seco-acid 36 to a solution of DEAD (7.7 equiv) and triphenylphosphine (7.5
  • formation of compound 92, which was reduced to the corresponding alcohol and then converted into the bromide 94. Ozonolysis followed by reaction with triphenylphosphine gave the corresponding phosphonium salt 96, which was subjected to different conditions for the intramolecular Wittig reaction. The best
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Published 29 Mar 2023

Group 13 exchange and transborylation in catalysis

  • Dominic R. Willcox and
  • Stephen P. Thomas

Beilstein J. Org. Chem. 2023, 19, 325–348, doi:10.3762/bjoc.19.28

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  • [85][88][89][97][101][105][106][107][108][109]. The aluminium-catalysed hydroboration of CO2 was reported by Fontaine using tris(triphenylphosphine)aluminium as the catalyst and HBcat as the terminal reductant [110]. So et al. reported the bis(phosphoranyl)methanido aluminium hydride-catalysed
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Published 21 Mar 2023

Continuous flow synthesis of 6-monoamino-6-monodeoxy-β-cyclodextrin

  • János Máté Orosz,
  • Dóra Ujj,
  • Petr Kasal,
  • Gábor Benkovics and
  • Erika Bálint

Beilstein J. Org. Chem. 2023, 19, 294–302, doi:10.3762/bjoc.19.25

Graphical Abstract
  • Staudinger reduction using triphenylphosphine (PPh3) and N3-β-CD (3) in DMF has been the most popular method for the synthesis of NH2-β-CD (4) since its first publication by Bonnet et al. [46]. This is despite the fact, that PPh3 and its oxidized product (triphenylphosphine oxide) form complexes with β-CD
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Published 09 Mar 2023

Revisiting the bromination of 3β-hydroxycholest-5-ene with CBr4/PPh3 and the subsequent azidolysis of the resulting bromide, disparity in stereochemical behavior

  • Christian Schumacher,
  • Jas S. Ward,
  • Kari Rissanen,
  • Carsten Bolm and
  • Mohamed Ramadan El Sayed Aly

Beilstein J. Org. Chem. 2023, 19, 91–99, doi:10.3762/bjoc.19.9

Graphical Abstract
  • C3 hydroxy of 1 is activated. Deprotonation of 10 at C2 with bromide as base provides diene 9 as the minor product. Bromide 4 is formed via cyclopropyl cation 11, which is generated from 10 by loss of triphenylphosphine oxide being supported by involvement of the Δ5 π-bond electrons from the α-face
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Published 27 Jan 2023

NaI/PPh3-catalyzed visible-light-mediated decarboxylative radical cascade cyclization of N-arylacrylamides for the efficient synthesis of quaternary oxindoles

  • Dan Liu,
  • Yue Zhao and
  • Frederic W. Patureau

Beilstein J. Org. Chem. 2023, 19, 57–65, doi:10.3762/bjoc.19.5

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  • ethers and N-heteroarenes by using a novel catalytic system based on sodium iodide (NaI) and triphenylphosphine (PPh3), suggested to function as an electron donor–acceptor (EDA) complex [55][56][57][58][59][60]. Compared to previously reported radical reactions, this novel catalytic system has the key
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Published 16 Jan 2023

Improving the accuracy of 31P NMR chemical shift calculations by use of scaling methods

  • William H. Hersh and
  • Tsz-Yeung Chan

Beilstein J. Org. Chem. 2023, 19, 36–56, doi:10.3762/bjoc.19.4

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  • use of the locally dense basis set approach, in which the larger pcS-3 basis set was used on phosphorus and the smaller pcS-2 basis set was then used on all the other atoms, allowed the computation of chemical shifts for a variety of benchmark compounds up to 35-atom triphenylphosphine oxide
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Published 10 Jan 2023

Preparation of β-cyclodextrin-based dimers with selectively methylated rims and their use for solubilization of tetracene

  • Konstantin Lebedinskiy,
  • Volodymyr Lobaz and
  • Jindřich Jindřich

Beilstein J. Org. Chem. 2022, 18, 1596–1606, doi:10.3762/bjoc.18.170

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  • kind of reaction engaging the azido group in the CD chemistry is the phosphine imide reaction [30][31]. This transformation involves triphenylphosphine and carbon dioxide to convert azide into isocyanate [31], allowing coupling with amines or other nucleophile groups. It is interesting to note that the
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Published 25 Nov 2022

Simple synthesis of multi-halogenated alkenes from 2-bromo-2-chloro-1,1,1-trifluoroethane (halothane)

  • Yukiko Karuo,
  • Atsushi Tarui,
  • Kazuyuki Sato,
  • Kentaro Kawai and
  • Masaaki Omote

Beilstein J. Org. Chem. 2022, 18, 1567–1574, doi:10.3762/bjoc.18.167

Graphical Abstract
  • functionalized enyne structure that will be useful in various molecular transformations [27][28][29]. On the basis of a previous report, Sonogashira cross-coupling of 2 with trimethylsilylacetylene was performed with a bis(triphenylphosphine)palladium(II) dichloride. The reaction proceeded smoothly to give
  • ), 153.9; 19F NMR (376 MHz, CDCl3) δ −80.5 (s, 1F), −80.6 (s, 1F); EIMS m/z: 250, 252 [M]+; HREIMS: [M]+ calcd for C8H5BrClFO, 249.9196, 251.9176; found, 249.9202, 251.9172. (3-Chloro-4-fluoro-4-phenoxybut-3-en-1-yn-1-yl)trimethylsilane (7): To a solution of 2a (0.5 mmol), bis(triphenylphosphine)palladium
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Published 21 Nov 2022

An alternative C–P cross-coupling route for the synthesis of novel V-shaped aryldiphosphonic acids

  • Stephen J. I. Shearan,
  • Enrico Andreoli and
  • Marco Taddei

Beilstein J. Org. Chem. 2022, 18, 1518–1523, doi:10.3762/bjoc.18.160

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  • catalyst, tetrakis(triphenylphosphine)palladium(0), was introduced by Hirao and co-workers, which allowed for the lowering of the reaction temperature to approximately 90 °C [29][30][31]. In this work, we have developed an alternative experimental protocol to perform the Ni-catalyzed C–P cross-coupling
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Published 07 Nov 2022

Modular synthesis of 2-furyl carbinols from 3-benzyldimethylsilylfurfural platforms relying on oxygen-assisted C–Si bond functionalization

  • Sebastien Curpanen,
  • Per Reichert,
  • Gabriele Lupidi,
  • Giovanni Poli,
  • Julie Oble and
  • Alejandro Perez-Luna

Beilstein J. Org. Chem. 2022, 18, 1256–1263, doi:10.3762/bjoc.18.131

Graphical Abstract
  • , given that the cross-coupling product 21 was obtained in only 40% yield (along with 23% of 22) in the absence of P(OEt)3 (Table 1, entry 5). The solution was the replacement of triethylphosphite by triphenylphosphine, which allowed to suppress the formation of the protodesilylated product and to obtain
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Published 16 Sep 2022

Molecular diversity of the base-promoted reaction of phenacylmalononitriles with dialkyl but-2-ynedioates

  • Hui Zheng,
  • Ying Han,
  • Jing Sun and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2022, 18, 991–998, doi:10.3762/bjoc.18.99

Graphical Abstract
  • reaction of phenacyl bromide, malononitrile, dialkyl but-2-ynedioate, and triphenylphosphine has been already reported, in which diethyl 3-phenyl-5,5-dicyanocyclopent-2-ene-1,2-dicarboxylates were produced by further elimination of a hydroxy group [30]. In the present reaction, the hydroxy group is still
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Published 08 Aug 2022

Tri(n-butyl)phosphine-promoted domino reaction for the efficient construction of spiro[cyclohexane-1,3'-indolines] and spiro[indoline-3,2'-furan-3',3''-indolines]

  • Hui Zheng,
  • Ying Han,
  • Jing Sun and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2022, 18, 669–679, doi:10.3762/bjoc.18.68

Graphical Abstract
  • and 2 in Table 1). Additionally, no reaction was observed when triphenylphosphine was used as catalyst (Table 1, entry 3). However, in the presence of tri(n-butyl)phosphine, the reaction in methylene dichloride, chloroform, and toluene at room temperature gave the expected functionalized spiro
  • triphenylphosphine. It should be pointed out that the synthesis of polysubstituted cyclohexanones was reported by a tri(n-butyl)phosphine-catalyzed reaction of 1,4-dien-3-ones with 2-aryl-1,1-dicyanoalkenes [36]. At higher temperature (50 °C), the yield of the product 3a increased to 40% (in CH2Cl2), 65% (in toluene
  • acted not only as a catalyst. It was also noticed that when triphenylphosphine was used instead of tri(n-butyl)phosphine, the expected product was not obtained. Under the optimized reaction conditions, we next investigated the scope of the reaction by using various substituted ethyl isatylidene
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Published 14 Jun 2022

Synthesis of sulfur karrikin bioisosteres as potential neuroprotectives

  • Martin Pošta,
  • Václav Zima,
  • Lenka Poštová Slavětínská,
  • Marika Matoušová and
  • Petr Beier

Beilstein J. Org. Chem. 2022, 18, 549–554, doi:10.3762/bjoc.18.57

Graphical Abstract
  • closure (Scheme 1). A plausible mechanism for the cyclization of compounds 7 is the Darzens reaction to episulfide, followed by Barton–Kellogg-type reaction with triphenylphosphine and elimination of triphenylphosphine sulfide. Compound 8 showed lower germination activity than KAR1 [22], but achieved IC50
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Published 16 May 2022

Menadione: a platform and a target to valuable compounds synthesis

  • Acácio S. de Souza,
  • Ruan Carlos B. Ribeiro,
  • Dora C. S. Costa,
  • Fernanda P. Pauli,
  • David R. Pinho,
  • Matheus G. de Moraes,
  • Fernando de C. da Silva,
  • Luana da S. M. Forezi and
  • Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 381–419, doi:10.3762/bjoc.18.43

Graphical Abstract
  • , menadione was obtained in 90% yield in 5 hours [89]. Another route was developed by Murahashi and co-workers that used p-cresol as synthetic precursor [90]. First, p-cresol, in the presence of tert-butyl hydroperoxide, was oxidized to 4-methyl-4-tert-butyldioxycyclohexadienone using tris(triphenylphosphine
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Published 11 Apr 2022

New efficient synthesis of polysubstituted 3,4-dihydroquinazolines and 4H-3,1-benzothiazines through a Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution sequence

  • Long Zhao,
  • Mao-Lin Yang,
  • Min Liu and
  • Ming-Wu Ding

Beilstein J. Org. Chem. 2022, 18, 286–292, doi:10.3762/bjoc.18.32

Graphical Abstract
  • isocyanides 3 produced the azide intermediates 4, which were treated sequentially with triphenylphosphine, isocyanates (or CS2), and secondary amines to give polysubstituted 3,4-dihydroquinazolines 8 and 4H-3,1-benzothiazines 11 in good overall yields through consecutive Passerini/Staudinger/aza-Wittig
  • . Compound 4a was then allowed to react with triphenylphosphine in CH2Cl2 at room temperature for 2 h to produce the iminophosphorane 5a by Staudinger reaction. Aza-Wittig reaction of 5a with phenyl isocyanate generated carbodiimide 6a, which was then treated with diethylamine to form the guanidine
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Published 04 Mar 2022

Synthesis and late stage modifications of Cyl derivatives

  • Phil Servatius and
  • Uli Kazmaier

Beilstein J. Org. Chem. 2022, 18, 174–181, doi:10.3762/bjoc.18.19

Graphical Abstract
  • ozonide formed during the reaction [57]. Consequently, no PPh3 or Me2S was required to obtain the crude aldehyde. Subsequent addition of a Wittig ylide gave access to a cyclopeptide with an α,β-unsaturated ester side chain as a (E/Z) mixture. Unfortunately, this compound contained triphenylphosphine oxide
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Published 04 Feb 2022

Selective sulfonylation and isonitrilation of para-quinone methides employing TosMIC as a source of sulfonyl group or isonitrile group

  • Chuanhua Qu,
  • Run Huang,
  • Yong Li,
  • Tong Liu,
  • Yuan Chen and
  • Guiting Song

Beilstein J. Org. Chem. 2021, 17, 2822–2831, doi:10.3762/bjoc.17.193

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  • acids via a triphenylphosphine-mediated deoxygenation process, followed by reaction with sulfonylated diarylmethane 3b to obtain diarylmethane ketone derivatives 6 and 7 [53]. To gain mechanistic insight into this C–S-bond cleavage sulfonylation reaction, some control experiments were conducted (Scheme
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Published 02 Dec 2021

Silica gel and microwave-promoted synthesis of dihydropyrrolizines and tetrahydroindolizines from enaminones

  • Robin Klintworth,
  • Garreth L. Morgans,
  • Stefania M. Scalzullo,
  • Charles B. de Koning,
  • Willem A. L. van Otterlo and
  • Joseph P. Michael

Beilstein J. Org. Chem. 2021, 17, 2543–2552, doi:10.3762/bjoc.17.170

Graphical Abstract
  • [57][58][59][60][61][62][63][64][65]. Results are summarized in Table 2. Triphenylphosphine and triethyl phosphite could be used interchangeably in the sulfur extrusion step. However, in most cases the co-elution of enaminones 15 with phosphorus-derived byproducts during chromatographic purification
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Published 13 Oct 2021

Development of N-F fluorinating agents and their fluorinations: Historical perspective

  • Teruo Umemoto,
  • Yuhao Yang and
  • Gerald B. Hammond

Beilstein J. Org. Chem. 2021, 17, 1752–1813, doi:10.3762/bjoc.17.123

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  • fluorination of pyridine or 2-fluoropyridine in anhydrous hydrogen fluoride [17][18] (Scheme 2). Not surprisingly, 1-1 did not become a popular reagent. In 1967, Banks et al. reported reactions of 1-1 with piperidine and triphenylphosphine, -arsine, and -stibine (Scheme 3, entries 1 and 2) [19]. The former
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Published 27 Jul 2021

Electron-rich triarylphosphines as nucleophilic catalysts for oxa-Michael reactions

  • Susanne M. Fischer,
  • Simon Renner,
  • A. Daniel Boese and
  • Christian Slugovc

Beilstein J. Org. Chem. 2021, 17, 1689–1697, doi:10.3762/bjoc.17.117

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  • triphenylphosphine (TPP) in catalyzing oxa-Michael additions. A matrix consisting of three differently strong Michael acceptors and four alcohols of varying acidity was used to assess the activity of the three catalysts. All test reactions were performed with 1 mol % catalyst loading, under solvent-free conditions
  • -Michael addition. Triphenylphosphine (TPP), (4-methoxyphenyl)diphenylphosphine (MMTPP) and tris(4-trimethoxyphenyl)phosphine (TMTPP). The catalysts were investigated in the reaction of four different Michael acceptors with four different alcohols. In the oxa-Michael addition, the zwitterion i, initially
  • by triphenylphosphine (TPP), (4-methoxyphenyl)diphenylphosphine (MMTPP), and tris(4-methoxyphenyl)phosphine (TMTPP). Reaction conditions: 1 equiv Michael acceptor, 2 equiv alcohol (in case of 3, 3 equiv alcohol), 1 mol % catalyst (with respect to the Michael acceptor), 1 h and 24 h (bars above grey
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Published 21 Jul 2021

Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

  • Nikita Brodyagin,
  • Martins Katkevics,
  • Venubabu Kotikam,
  • Christopher A. Ryan and
  • Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

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Published 19 Jul 2021

2,4-Bis(arylethynyl)-9-chloro-5,6,7,8-tetrahydroacridines: synthesis and photophysical properties

  • Najeh Tka,
  • Mohamed Adnene Hadj Ayed,
  • Mourad Ben Braiek,
  • Mahjoub Jabli,
  • Noureddine Chaaben,
  • Kamel Alimi,
  • Stefan Jopp and
  • Peter Langer

Beilstein J. Org. Chem. 2021, 17, 1629–1640, doi:10.3762/bjoc.17.115

Graphical Abstract
  • using 0.6 mol % of tetrakis(triphenylphosphine)palladium(0) and 1.2 mol % of copper iodide (Scheme 2, Table 1). The reaction proceeded chemoselectively at the two carbon–bromine bonds giving 2,4-bis(phenylethynyl)-9-chloro-5,6,7,8-tetrahydroacridine (4a). This result was not entirely predictable, as the
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Published 16 Jul 2021

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

  • Guido Gambacorta,
  • James S. Sharley and
  • Ian R. Baxendale

Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90

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Published 18 May 2021

Recent advances in palladium-catalysed asymmetric 1,4–additions of arylboronic acids to conjugated enones and chromones

  • Jan Bartáček,
  • Jan Svoboda,
  • Martin Kocúrik,
  • Jaroslav Pochobradský,
  • Alexander Čegan,
  • Miloš Sedlák and
  • Jiří Váňa

Beilstein J. Org. Chem. 2021, 17, 1048–1085, doi:10.3762/bjoc.17.84

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  • systematic study of phosphine-based Pd complexes was done by Wong et al. in 2014. The palladacycle PdL6 was used in combination with triphenylphosphine and K3PO4 acting as a base. The highest enantioselectivity of 99% ee of a model addition of phenylboronic acid to 2-cyclohexenone was achieved in dioxane as
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Published 10 May 2021
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