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Search for "phosphines" in Full Text gives 106 result(s) in Beilstein Journal of Organic Chemistry.

Controlled decomposition of SF6 by electrochemical reduction

  • Sébastien Bouvet,
  • Bruce Pégot,
  • Stéphane Sengmany,
  • Erwan Le Gall,
  • Eric Léonel,
  • Anne-Marie Goncalves and
  • Emmanuel Magnier

Beilstein J. Org. Chem. 2020, 16, 2948–2953, doi:10.3762/bjoc.16.244

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  • reactive, corrosive and toxic [12]. Recent and really impressive works were devoted to the decomposition of sulfur hexafluoride using stoichiometric or catalytic amounts of metals (Rh, Ni, Pt) [13][14][15][16]. Organic derivatives (phosphines or bipyridine) proved efficient tools for the selective
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Published 01 Dec 2020

Recent synthesis of thietanes

  • Jiaxi Xu

Beilstein J. Org. Chem. 2020, 16, 1357–1410, doi:10.3762/bjoc.16.116

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  • transform 1,3-diols 62 into the precursors of γ-mercaptoalkanols with dibenzoxazol-2-yl disulfide (63) and phosphines. They reacted primary or secondary 1,3-diols 62 with disulfide 63 in the presence of Bu3P or Ph3P to selectively synthesize 2-(3-hydroxyalkylthio)benzoxazoles 64. These were treated with KH
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Published 22 Jun 2020

Copper catalysis with redox-active ligands

  • Agnideep Das,
  • Yufeng Ren,
  • Cheriehan Hessin and
  • Marine Desage-El Murr

Beilstein J. Org. Chem. 2020, 16, 858–870, doi:10.3762/bjoc.16.77

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  • applications in various synthetic fields by utilizing the ability of copper to sustain mono- and bielectronic elementary steps. Further to the development of well-defined copper complexes with classical ligands such as phosphines and N-heterocyclic carbenes, a new and fast-expanding area of research is
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Published 24 Apr 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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  • , Pietermaritzburg 3201, South Africa 10.3762/bjoc.16.35 Abstract Diverse P,N-phosphine ligands reported to date have performed exceptionally well as auxiliary ligands in organometallic catalysis. Phosphines bearing 2-pyridyl moieties prominently feature in literature as compared to phosphines with five-membered N
  • -heterocyclic phosphines; Introduction Phosphines constitute a large percentage of ligands in organometallic chemistry and over the years, they have received enormous attention. The main interest towards this class of compounds is attributed to aspects such as, the good electron-donating ability of the
  • coordination [12]. Thus, their use in catalysis is the basis of this review article with the main focus on the synthesis of N-heterocyclic phosphines. The presence of soft donor atoms such as phosphorus results in the formation of hemilabile ligands. These are multidentate ligands having hard P-donor and soft
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Published 12 Mar 2020

Copper-catalyzed enantioselective conjugate addition of organometallic reagents to challenging Michael acceptors

  • Delphine Pichon,
  • Jennifer Morvan,
  • Christophe Crévisy and
  • Marc Mauduit

Beilstein J. Org. Chem. 2020, 16, 212–232, doi:10.3762/bjoc.16.24

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  • ratios were obtained (51:49 to 97:3). Of note, chiral phosphines were also screened, but without any improvement of selectivity. Furthermore, this methodology was then efficiently applied to the total synthesis of several bisabolane sesquiterpenes, which exhibited anticancer and antimicrobial activities
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Published 17 Feb 2020

Chiral terpene auxiliaries V: Synthesis of new chiral γ-hydroxyphosphine oxides derived from α-pinene

  • Anna Kmieciak and
  • Marek P. Krzemiński

Beilstein J. Org. Chem. 2019, 15, 2493–2499, doi:10.3762/bjoc.15.242

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  • site providing a trans relationship between the hydroxy and the phosphine substituents. Keywords: isopinocamphone; monoterpenes; phosphines; [2,3]-sigmatropic rearrangement; verbanone; Introduction Chiral phosphorus compounds, despite many years of research, still enjoy unflagging interest of many
  • ], conjugated additions to enones [7], and allylic alkylations [8][9]. Another direction of research is the use of phosphines in organocatalysis [10][11] and bifunctional catalysis [12]. Several methods were developed to introduce the phosphine functionality to organic molecules. The reaction of organometallics
  • with chlorophosphines, the reaction of metal phosphides with haloalkanes, and transition-metal-catalyzed cross-coupling reactions to form C–P bonds are the most widely used methods for the synthesis of phosphines [13][14]. Since phosphines are easily oxidized to phosphine oxides, the addition of
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Published 22 Oct 2019

Sigmatropic rearrangements of cyclopropenylcarbinol derivatives. Access to diversely substituted alkylidenecyclopropanes

  • Guillaume Ernouf,
  • Jean-Louis Brayer,
  • Christophe Meyer and
  • Janine Cossy

Beilstein J. Org. Chem. 2019, 15, 333–350, doi:10.3762/bjoc.15.29

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  • chiral phosphines possessing an alkylidenecyclopropane backbone [34]. The starting cyclopropenylcarbinols were readily prepared by addition of the corresponding cyclopropenyl organolithium reagents, generated in situ by treatment of 1,1,2-tribromocyclopropane with n-butyllithium (2 equiv) [35], to
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Published 05 Feb 2019

Mechanistic studies of an L-proline-catalyzed pyridazine formation involving a Diels–Alder reaction with inverse electron demand

  • Anne Schnell,
  • J. Alexander Willms,
  • S. Nozinovic and
  • Marianne Engeser

Beilstein J. Org. Chem. 2019, 15, 30–43, doi:10.3762/bjoc.15.3

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  • introduced into the analyte molecules, usually in the form of alkylated amines or phosphines [5][6]. The charge-tag can be located either within the substrate [23][24][25] or the catalyst [18][26][27]. As a result, all species containing the charge-tag will have a similarly high ESI response [6][25] while
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Published 03 Jan 2019

Photocatalyic Appel reaction enabled by copper-based complexes in continuous flow

  • Clémentine Minozzi,
  • Jean-Christophe Grenier-Petel,
  • Shawn Parisien-Collette and
  • Shawn K. Collins

Beilstein J. Org. Chem. 2018, 14, 2730–2736, doi:10.3762/bjoc.14.251

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  • bromide. From the results, none of the homoleptic complexes promoted the alcohol-to-halide conversion (1→2, see the light blue entries in the front row of Figure 3). While many of the heteroleptic complexes promoted the reaction, some trends were apparent. In general, amongst the phosphines the dppf-based
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Published 30 Oct 2018

Non-metal-templated approaches to bis(borane) derivatives of macrocyclic dibridgehead diphosphines via alkene metathesis

  • Tobias Fiedler,
  • Michał Barbasiewicz,
  • Michael Stollenz and
  • John A. Gladysz

Beilstein J. Org. Chem. 2018, 14, 2354–2365, doi:10.3762/bjoc.14.211

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  • . Oxidations that lead to the corresponding dibridgehead diphosphine dioxides (O=)P((CH2)n)3P(=O) have exhibited promise, but purification has been problematic [24]. Indeed, phosphine oxides are everyday precursors to phosphines, so we have considered various non-metal-templated routes to 2·2(=O), 3·2(=O), and
  • phosphine boranes of alkene containing phosphines. The first involves the monophosphorus precursor H3B·P((CH2)6CH=CH2)3 (1·BH3) [31], and the second a diphosphorus precursor in which one of the methylene chains linking the two phosphorus atoms has already been installed. The advantages and limitations of
  • adducts of primary phosphines can be doubly deprotonated, and that the resulting phosphorus dianions can be bis(alkylated) [45][46][47]. Thus, the diphosphine 10 and H3B·SMe2 were reacted to give the diphosphine diborane H2(H3B)P((CH2)14)P(BH3)H2 (10·2BH3) as a white solid in 87% yield. A subsequent
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Published 07 Sep 2018

D-Fructose-based spiro-fused PHOX ligands: synthesis and application in enantioselective allylic alkylation

  • Michael R. Imrich,
  • Jochen Kraft,
  • Cäcilia Maichle-Mössmer and
  • Thomas Ziegler

Beilstein J. Org. Chem. 2018, 14, 2082–2089, doi:10.3762/bjoc.14.182

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  • nitrile is slower compared to the unstabilized 9b. The Stoltz and co-workers reported the preparation of a series of PHOX ligands using Buchwald’s copper-catalyzed C–P bond construction [48][49]. This reaction allows the Ullmann coupling of aryl halides with secondary phosphines to afford tertiary
  • phosphines. We chose Stoltz’s protocol to introduce the diphenylphosphine moiety to our β-configurated bromoaryloxazolines 10a–i as well as to oxazoline 11i due to the fact that the peracetylated sugar could be obtained as an α-anomer in relatively high yield. The reaction afforded the spiro-fused PHOX
  • phosphines can be used as nucleophiles for deacetylation reactions [50][51]. We suppose that the lower yields of 5f–i and 14a can be explained by partial or full deacylation of the protective groups. This explanation is also in good accordance with the fact that the yield of the ester protected PHOX ligand
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Published 08 Aug 2018

Thiocarbonyl-enabled ferrocene C–H nitrogenation by cobalt(III) catalysis: thermal and mechanochemical

  • Santhivardhana Reddy Yetra,
  • Zhigao Shen,
  • Hui Wang and
  • Lutz Ackermann

Beilstein J. Org. Chem. 2018, 14, 1546–1553, doi:10.3762/bjoc.14.131

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  • and Discussion We initiated our studies by probing various reaction conditions for the envisioned C–H amidation of ferrocene 1a (Table 1). Among a variety of ligands, N-heterocyclic carbenes and phosphines provided unsatisfactory results (Table 1, entries 1–3), while the product 3aa was formed when
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Published 25 Jun 2018

Three-component coupling of aryl iodides, allenes, and aldehydes catalyzed by a Co/Cr-hybrid catalyst

  • Kimihiro Komeyama,
  • Shunsuke Sakiyama,
  • Kento Iwashita,
  • Itaru Osaka and
  • Ken Takaki

Beilstein J. Org. Chem. 2018, 14, 1413–1420, doi:10.3762/bjoc.14.118

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  • of several phosphines and pyridine-type ligands, the latter ligands were found to be the most effective for use in the coupling reaction. Consequently, we found that iminopyridine L3 was the best choice of ligand, and when used, it resulted in the three-component product 4a being obtained in 69
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Published 11 Jun 2018

Recent applications of chiral calixarenes in asymmetric catalysis

  • Mustafa Durmaz,
  • Erkan Halay and
  • Selahattin Bozkurt

Beilstein J. Org. Chem. 2018, 14, 1389–1412, doi:10.3762/bjoc.14.117

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  • enantiomerically pure (S)-(2-diphenylthiophosphinoferrocenyl)methanol. Deprotection of the thiophosphine unit(s) by tris(dimethylamino)phosphine gave chiral calixarene phosphines 27–29 bearing ferrocenyl substituents on the lower rim in high yields. Calixarene-derived mono(ferrocenylphosphine) ligands 27 and 28
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Published 08 Jun 2018

Cobalt-catalyzed directed C–H alkenylation of pivalophenone N–H imine with alkenyl phosphates

  • Wengang Xu and
  • Naohiko Yoshikai

Beilstein J. Org. Chem. 2018, 14, 709–715, doi:10.3762/bjoc.14.60

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  • temperature. While monodentate phosphines such as PPh3 and PCy3 were entirely ineffective (Table 1, entries 1 and 2), common bulky NHC precursors such as 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride (IMes·HCl) and 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPr·HCl) promoted the coupling
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Published 28 Mar 2018

Heterogeneous Pd catalysts as emulsifiers in Pickering emulsions for integrated multistep synthesis in flow chemistry

  • Katharina Hiebler,
  • Georg J. Lichtenegger,
  • Manuel C. Maier,
  • Eun Sung Park,
  • Renie Gonzales-Groom,
  • Bernard P. Binks and
  • Heidrun Gruber-Woelfler

Beilstein J. Org. Chem. 2018, 14, 648–658, doi:10.3762/bjoc.14.52

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  • are utilised. The employment of a variety of different ligands such as phosphines, amines and carbenes allows precise tuning of the properties of homogeneous Pd catalysts, which led to significant improvements in turn over number (TON), reaction rates, enantioselectivity as well as catalyst robustness
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Published 19 Mar 2018

Copper-catalyzed asymmetric methylation of fluoroalkylated pyruvates with dimethylzinc

  • Kohsuke Aikawa,
  • Kohei Yabuuchi,
  • Kota Torii and
  • Koichi Mikami

Beilstein J. Org. Chem. 2018, 14, 576–582, doi:10.3762/bjoc.14.44

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  • ) groups in good-to-high yields and enantioselectivities. Axial backbones and substituents on phosphorus atoms of chiral phosphine ligands critically influence the enantioselectivity. Moreover, the methylation of simple perfluoroalkylated ketones is found to be facilitated by only chiral phosphines without
  • product (25% yield, 0% ee). Interestingly, the use of only BINAP without CuTC led to higher reactivity and enantioselectivity (54% yield, 8% ee), while BTFM-Garphos decreased the reactivity (7% yield, 8% ee). After screening of phosphines, DTB-MeO-BIPHEP was found to smoothly catalyze the asymmetric
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Published 07 Mar 2018

Vinylphosphonium and 2-aminovinylphosphonium salts – preparation and applications in organic synthesis

  • Anna Kuźnik,
  • Roman Mazurkiewicz and
  • Beata Fryczkowska

Beilstein J. Org. Chem. 2017, 13, 2710–2738, doi:10.3762/bjoc.13.269

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  • anticancer drugs, antioxidants, or functional probes into the mitochondria [5][6][7][8]. Review 1. Synthesis of vinylphosphonium salts 1.1. Alkylation of phosphines with alkyl halides One of the most common methods for the preparation of vinylphosphonium salts 1 is the quaternization of vinylphosphines with
  • Wehman (Scheme 4) [10]. Vinylphosphonium salts can also be prepared by alkylation of phosphines (usually triphenylphosphine) with allyl halide derivatives and isomerization of allylphosphonium salts 4 thus obtained under the influence of bases such as triethylamine or sodium carbonate (Scheme 5) [11][12
  • closure and the formation of dialkyl 2-(alkylamino)-5-aryl-3,4-furanedicarboxylate 124 in a yield of 69–88% (Scheme 69). The reaction was carried out for several hours at room temperature in anhydrous CH2Cl2 [81]. Recently, an interesting one-pot condensation of acetylenedicarboxylates with phosphines and
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Published 15 Dec 2017

Pd(OAc)2/Ph3P-catalyzed dimerization of isoprene and synthesis of monoterpenic heterocycles

  • Dominik Kellner,
  • Maximilian Weger,
  • Andrea Gini and
  • Olga García Mancheño

Beilstein J. Org. Chem. 2017, 13, 1807–1815, doi:10.3762/bjoc.13.175

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  • Beller and co-workers (Scheme 1, reaction 2) [33]. The use of NHCs proved to be the key, since the more accessible monodentated phosphorus ligands such as triphenyl (Ph3P) or tricyclohexyl (Cy3P) phosphines showed a significant lower efficiency and different selectivity with the same palladium source Pd
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Published 29 Aug 2017

Development of a method for the synthesis of 2,4,5-trisubstituted oxazoles composed of carboxylic acid, amino acid, and boronic acid

  • Kohei Yamada,
  • Naoto Kamimura and
  • Munetaka Kunishima

Beilstein J. Org. Chem. 2017, 13, 1478–1485, doi:10.3762/bjoc.13.146

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  • Suzuki–Miyaura coupling between 5-(triazinyloxy)oxazole 3aa and phenylboronic acid (4a, Table 2). As expected, the desired trisubstituted oxazole 5aaa was obtained in 21% yield (Table 2, entry 1). The use of different bidentate (dppp) or monodentate (PCy3) phosphines as ligands for the Ni catalyst
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Published 27 Jul 2017

Construction of highly enantioenriched spirocyclopentaneoxindoles containing four consecutive stereocenters via thiourea-catalyzed asymmetric Michael–Henry cascade reactions

  • Yonglei Du,
  • Jian Li,
  • Kerong Chen,
  • Chenglin Wu,
  • Yu Zhou and
  • Hong Liu

Beilstein J. Org. Chem. 2017, 13, 1342–1349, doi:10.3762/bjoc.13.131

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  • strategies with chiral transition metals [27][28][29][30][31][32][33], organocatalysts such as secondary amines [34][35][36], nucleophilic phosphines [26][37][38][39][40][41][42][43][44], tertiary amines [45], N-heterocyclic carbenes (NHCs) [46][47][48], and cinchona alkaloid derivatives [25][28][49][50
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Published 07 Jul 2017

Glyco-gold nanoparticles: synthesis and applications

  • Federica Compostella,
  • Olimpia Pitirollo,
  • Alessandro Silvestri and
  • Laura Polito

Beilstein J. Org. Chem. 2017, 13, 1008–1021, doi:10.3762/bjoc.13.100

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  • simply mixing at room temperature Au3+ salts and thio-glucoside as reducing and stabilizing agents, without the addition of NaBH4 [19]. The two-step synthetic procedure consists in the initial synthesis of AuNPs stabilized by temporary compounds (i.e., citrates, amines or phosphines), followed by the
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Published 24 May 2017

Catalytic Wittig and aza-Wittig reactions

  • Zhiqi Lao and
  • Patrick H. Toy

Beilstein J. Org. Chem. 2016, 12, 2577–2587, doi:10.3762/bjoc.12.253

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  • covers the field of related catalytic aza-Wittig reactions that are catalyzed by both phosphine oxides and phosphines. Keywords: aza-Wittig reactions; catalysis; phosphines; phosphine oxides; reduction; silanes; Wittig reactions; Introduction The Wittig reaction is a venerable transformation for
  • impediment to the development of phosphine-catalyzed Wittig reactions was the stability of phosphine oxides and the harsh reaction conditions generally required to reduce them to the corresponding phosphines were thought to be incompatible with various necessary reactants and reagents, and the desired
  • reaction (Scheme 8) [22]. This reaction involved the intramolecular cyclization of 27 to form 28. A variety of phosphines were examined as the catalyst, and (S,S)-29 ((S,S)-Me-DuPhos, 0.1 equivalent) was found to provide the best combination of reactivity and stereoselectivity (39% yield, 62% ee). In these
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Published 30 Nov 2016

Protonated paramagnetic redox forms of di-o-quinone bridged with p-phenylene-extended TTF: A EPR spectroscopy study

  • Nikolay O. Chalkov,
  • Vladimir K. Cherkasov,
  • Gleb A. Abakumov,
  • Andrey G. Starikov and
  • Viacheslav A. Kuropatov

Beilstein J. Org. Chem. 2016, 12, 2450–2456, doi:10.3762/bjoc.12.238

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  • dissolves in solutions of o-quinones [9][10][11]. This process is greatly accelerated by the presence of auxiliary ligands, such as phosphines or pyridines. But the oxidation of copper metal with a reduced protonated quinone, which is (1)H2 in fact, was observed for the first time. This process leads to the
  • reduction process of copper with (1)H2. The EPR signal corresponding to (1·−)H2 could be observed only if a chelating diphosphine was used as an auxiliary ligand in the reaction of copper with (1)H2. Most likely, phosphines such as dppe, dppb or dppfc provide better stability for the copper(I) ion in
  • solution due to chelation. It should be mentioned, that the reduction of (1)H2 with copper metal proceeds also in the presence of non-bridging phosphines, such as PPh3, but the radical anion species (1·−)H2 is stable only in the presence of a large counterion such as [Cu(dppe)2]+. The signal of the solvent
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Published 17 Nov 2016

Enantioconvergent catalysis

  • Justin T. Mohr,
  • Jared T. Moore and
  • Brian M. Stoltz

Beilstein J. Org. Chem. 2016, 12, 2038–2045, doi:10.3762/bjoc.12.192

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  • type I enantioconvergent catalysis was reported by Glueck for the preparation of enantioenriched P-chiral phosphines (Scheme 2) [17]. In this process, enantiopure Pd complex (R,R)-4 reacts with racemic phosphine 3 to form phosphido complexes 5 and 6. Although the rate of configurational inversion of
  • . Enantioconvergent synthesis of phosphines governed by Curtin–Hammett/Winstein–Holness kinetics (TMS = trimethylsilyl, Is = 2,4,6-triisopropylphenyl). Stoltz’ stereoablative oxindole functionalization. Fu’s type II enantioconvergent Cu-catalyzed photoredox reaction. Stereoablative enantioconvergent allylation and
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Published 16 Sep 2016
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