- Kinetico-mechanistic insights on the assembling dynamics of allyl-cornered metallacycles: The Pt-Npy bond is the keystone
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The square-like homo- and heterometallamacrocycles [{Pd(η3-2-Me-C3H4)(Ln)2}2{M(dppp)}2](CF3SO3)6 (dppp = 1,3-bis(diphenylphosphino)propane) and [
- Angurell, Inmaculada,Ferrer, Montserrat,Gutrrez, Albert,Martnez, Manuel,Rocamora, Merc,Rodguez, Laura,Rossell, Oriol,Lorenz, Yvonne,Engeser, Marianne
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- Self-Assembled, Highly Positively Charged, Allyl–Pd Crowns: Cavity-Pocket-Driven Interactions of Fluoroanions
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A series of dodecanuclear highly positively charged homo- and heterometallamacrocycles [{Pd(η3-2-Me-C3H4)}6(4-PPh2py)12{M2(tpbz)}3]18+ (M=Pd, Pt; tpbz=1,2,4,5-tetrakis(diphenylphosphanyl)benzene were synthesized by the quantitative self-assembly of {Pd(η3-2-Me-C3H4)}+, {M2(tpbz)}4+ and 4-PPh2py moieties in 2:1:4 molar ratio. The cationic assemblies were obtained as salts of different fluorinated anions with diverse sizes and electronic properties, namely BF4?, PF6?, SbF6? and CF3SO3?. The new crown-like metallamacrocycles showed remarkable differences in their NMR spectra due to the presence of the different counteranions. On the basis of the observed variations, the metallacycles have been tested as catalytic precursors in allylic alkylation reactions. The anion-dependent activity and selectivity has been analysed and compared with that of the corresponding monometallic allylic corners [Pd(η3-2-Me-C3H4)(4-PPh2py)2]X (X=BF4?, PF6?, SbF6?, CF3SO3?). DFT calculations have been employed in order to help to the interpretation of the experimental data and to model the anion–crown interactions.
- Engeser, Marianne,Ferrer, Montserrat,Gallen, Albert,Gutiérrez, Albert,Lorenz, Yvonne,Martínez, Manuel,Ruiz, Eliseo
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- Nickel(II) and Palladium(II) complexes of the small-bite-angle p-stereogenic diphosphine ligand MaxPHOS and Its monosulfide
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Coordination studies of the optically pure diphosphine ligand (t-Bu) 2P(NH)P(t-BuMe) (MaxPHOS) and its monosulfide with several Pd and Ni moieties are described. Treatment of a solution of MaxPHOS·HBF 4 with [M(acac)2] (M
- Grabulosa, Arnald,Doran, Sean,Brandariz, Guillem,Muller, Guillermo,Benet-Buchholz, Jordi,Riera, Antoni,Verdaguer, Xavier
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Read Online
- Iridium/ N-Heterocyclic Carbene Complex-Catalyzed Intermolecular Allylic Alkylation Reaction
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N-Heterocyclic carbenes (NHCs) were found to be suitable ligands in Ir-catalyzed intermolecular allylic alkylation reaction. In the presence of a catalyst derived from [Ir(dncot)Cl]2 (dncot = dinaphthocyclooctatetraene) and triazolium salt L7,
- Bao, Can-Can,Zheng, Dong-Song,Zhang, Xiao,You, Shu-Li
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p. 4763 - 4772
(2019/01/04)
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- Efficient stereochemical communication in phosphine-amine palladium-complexes: Exploration of N-substituent effects in coordination chemistry and catalysis
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Six-membered chelate complexes of type [Pd(1a-e)Cl2] (2a-e) and [Pd(1a-e)(η3-PhCHCHCHPh)]BF4 (3a-e) of a series of systematically varied chiral phosphine-amine ligands (S,S)-Ph2PCH(CH3)CH2C
- Farkas, Gergely,Császár, Zsófia,Stágel, Kristóf,Nemes, Evelin,Balogh, Szabolcs,Tóth, Imre,Bényei, Attila,Lendvay, Gy?rgy,Bakos, József
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p. 129 - 140
(2017/06/19)
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- Sugar-annulated oxazoline ligands: A novel Pd(II) complex and its application in allylic substitution
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Two novel carbohydrate-derived pyridyl (PYOX)- and cyclopropyl (CYBOX)-substituted oxazoline ligands were prepared from D-glucosamine hydrochloride and 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-β-D-glucopyranose hydrochloride in two steps, respectively. The sugar-annulated PYOX ligand formed a stable metal complex with Pd(II), which was fully characterized by NMR spectroscopy and X-ray crystallography. NMR and X-ray analysis revealed a change of the conformation in the sugar moiety upon complexation with the palladium(II) species. Both glycosylated ligands resulted in high asymmetric induction (up to 98% ee) upon application as chiral ligands in the Pd-catalyzed allylic alkylation of rac-1,3-diphenylallyl acetate with dimethyl malonate (Tsuji-Trost reaction). Both ligands provided mainly the (R)-enantiomer of the alkylation product.
- Kraft, Jochen,Mill, Katharina,Ziegler, Thomas
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- Palladium catalyzed direct benzylation/allylation of malonates with alcohols-: In situ C-O bond activation
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High step- and atom-economy are the endlessly pursued in organic and pharmaceutical syntheses. Herein, a new method for directly coupling benzyl/allyl alcohols with malonates via a palladium catalyzed Tsuji-Trost type reaction was developed. The reaction was carried out in an organic carbonate solvent which would activate alcohols in situ, replacing the traditional pre-synthesized carbonates. The new process demonstrated high efficiency, high selectivity and high generality. A wide variety of mono-substituted and bis-substituted malonates were selectively produced under different conditions, and this method represents a more step- and atom-economical and environmentally benign synthetic protocol.
- Cao, Xueqin,Zhang, Yugen
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supporting information
p. 2638 - 2641
(2016/05/24)
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- Containing dinaphthyl [1, 2-b; 5, 6-b '] chiral phosphine nitrogen skeleton and cyclooctatetraene π-ene propyl iridium complex, synthesis method and application
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The invention provides an optically pure pi-allyl iridium complex containing dinaphthyl [1,2-b;5,6-b'] cyclooctatetraene and a chiral phosphine nitrogen framework as well as a synthesizing method and application of the complex in an asymmetric allyl subst
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Paragraph 0628; 0629; 0630; 0631; 0632; 0633
(2017/09/19)
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- Palladium-Based Supramolecularly Regulated Catalysts for Asymmetric Allylic Substitutions
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Herein is reported the effect of different polyether binders (alkali metal, alkaline earth metal, and lanthanide salts) as regulation agents to enhance the catalytic properties of palladium complexes derived from enantiopure bisphosphite ligands in allyli
- Rovira, Laura,Fernández-Pérez, Héctor,Vidal-Ferran, Anton
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p. 528 - 533
(2016/03/01)
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- Conformational Preferences of a Tropos Biphenyl Phosphinooxazoline-a Ligand with Wide Substrate Scope
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Excellent enantioselectivities are observed in palladium-catalyzed allylic substitutions of a wide range of substrate types and nucleophiles using a bidentate ligand composed of oxazoline and chirally flexible biaryl phosphite elements. This unusually wid
- Bellini, Rosalba,Magre, Marc,Biosca, Maria,Norrby, Per-Ola,Pàmies, Oscar,Diéguez, Montserrat,Moberg, Christina
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p. 1701 - 1712
(2016/03/15)
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- Diphosphorus Ligands Containing a P-Stereogenic Phosphane and a Chiral Phosphite or Phosphorodiamidite – Evaluation in Pd-Catalysed Asymmetric Allylic Substitution Reactions
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The synthesis of 14 new optically pure C1-symmetric phosphane–phosphinite (1–4), phosphane–phosphite (5–9) and phosphane–phosphorodiamidite (10–14) ligands is reported. The ligands were prepared through the condensation of (2-hydroxyphenyl)phenylphosphanes PPh(2-PhOH)R (R = Me, tBu and Ph) with chlorodiisopropylphosphane (1 and 2), chlorodiphenylphosphane (3 and 4), the chlorodioxaphosphepine derived from both enantiomers of 1,1′-bi-2-naphthol (5–9) and the chlorodiazaphosphepine derived from both enantiomers of N,N′-dimethyl-1,1′-binaphthyl-2,2′-diamine (10–14) in the presence of a base. With these ligands, cationic Pd complexes of the type [Pd(η3-C4H7)(PP′)]PF6(Pd1–Pd14) were obtained and characterised; the crystal structures of Pd1, Pd2 and Pd13 were obtained. In solution, the complexes are present as mixtures of two diastereomers because of the lack of symmetry of the ligand and the presence of the methallyl group. The Pd complexes catalyse the allylic alkylation with dimethyl malonate and the amination with benzylamine of the model substrate rac-3-acetoxy-1,3-diphenyl-1-propene (I). For the alkylation, full conversions and good enantioselectivities (up to 96 % ee with Pd14) were observed.
- Clavero, Pau,Grabulosa, Arnald,Rocamora, Mercè,Muller, Guillermo,Font-Bardia, Mercè
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supporting information
p. 4054 - 4065
(2016/09/13)
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- Origins of Regioselectivity in Iridium Catalyzed Allylic Substitution
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Detailed studies on the origin of the regioselectivity for formation of branched products over linear products have been conducted with complexes containing the achiral triphenylphosphite ligand. The combination of iridium and P(OPh)3 was the first catalytic system shown to give high regioselectivity for the branched product with iridium and among the most selective for forming branched products among any combination of metal and ligand. We have shown the active catalyst to be generated from [Ir(COD)Cl]2 and P(OPh)3 by cyclometalation of the phenyl group on the ligand and have shown such species to be the resting state of the catalyst. A series of allyliridium complexes ligated by the resulting P,C ligand have been generated and shown to be competent intermediates in the catalytic system. We have assessed the potential impact of charge, metal-iridium bond length, and stability of terminal vs internal alkenes generated by attack at the branched and terminal positions of the allyl ligand, respectively. These factors do not distinguish the regioselectivity for attack on allyliridium complexes from that for attack on allylpalladium complexes. Instead, detailed computational studies suggest that a series of weak, attractive, noncovalent interactions, including interactions of H-bond acceptors with a vinyl C - H bond of the alkene ligand, favor formation of the branched product with the iridium catalyst. This conclusion underscores the importance of considering attractive interactions, as well as repulsive steric interactions, when seeking to rationalize selectivities.
- Madrahimov, Sherzod T.,Li, Qian,Sharma, Ankit,Hartwig, John F.
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p. 14968 - 14981
(2015/12/08)
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- Highly enantioselective alkylation of allyl acetates using tartrate-derived bioxazoline ligands
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Tartrate-derived bioxazoline ligands, which form a five-membered chelate ring with metals, were evaluated for use in the asymmetric allylic alkylation (AAA) reactions of various symmetrical and unsymmetrical allyl acetates. Excellent enantioselectivities
- Jayakumar, Samydurai,Prakash, Muthuraj,Balaraman, Kaluvu,Kesavan, Venkitasamy
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p. 606 - 615
(2014/02/14)
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- A bis(triazolecarboxamido) ligand for enantio- and regioselective molybdenum-catalyzed asymmetric allylic alkylation reactions
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A modular, enantiomerically pure bis(1H-1,2,3-triazole-4-carboxamide) has been assembled from N,N'-[(1R,2R)-cyclohexane-1,2-diyl]dipropiolamide through a copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction and evaluated as a ligand in the molybde
- Ozkal, Erhan,Pericas, Miquel A.
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supporting information
p. 711 - 717
(2014/04/03)
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- Synthesis of 1-[bis(trifluoromethyl)phosphine]-1'- oxazolinylferrocene ligands and their application in regio- and enantioselective Pd-catalyzed allylic alkylation of monosubstituted allyl substrates
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A class of novel, easily accessible and air-stable 1-[bis(trifluoromethyl) phosphine]-1'-oxazolinylferrocene ligands has been synthesized from ferrocene. It became apparent that these ligands can be used in the regio- and enantioselective Pd-catalyzed allylic alkylation of monosubstituted allyl substrates in a highly efficient manner. Excellent regio- and enantioselectivity could be obtained for a wide range of substrates.
- Lai, Zeng-Wei,Yang, Rong-Fei,Ye, Ke-Yin,Sun, Hongbin,You, Shu-Li
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supporting information
p. 1261 - 1266
(2014/06/24)
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- A simple diamine as ligand in iron-catalyzed regioselective allylic alkylation
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A simple and efficient diamine was found to be an efficient ligand for the iron-catalyzed regioselective allylic alkylation between various allyl carbonates and nucleophiles, affording excellent yields and good regioselectivity (up to 94% and >20:1).
- Yu, Chenguang,Zhou, Aihua,He, Jing
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p. 8627 - 8630
(2015/02/19)
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- Iridium-catalyzed allylic alkylation reaction with N-aryl phosphoramidite ligands: Scope and mechanistic studies
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A series of N-aryl phosphoramidite ligands has been synthesized and applied to iridium-catalyzed allylic alkylation reactions, offering high regio- and enantioselectivities for a wide variety of substrates. These ligands feature the synthetic convenience and good tolerance of the ortho-substituted cinnamyl carbonates. Mechanistic studies, including DFT calculations and X-ray crystallographic analyses of the (π-allyl)-Ir complexes, reveal that the active iridacycle is formed via C(sp2)-H bond activation.
- Liu, Wen-Bo,Zheng, Chao,Zhuo, Chun-Xiang,Dai, Li-Xin,You, Shu-Li
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supporting information; experimental part
p. 4812 - 4821
(2012/04/23)
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- C1-Symmetric carbohydrate diphosphite ligands for asymmetric Pd-allylic alkylation reactions. Study of the key Pd-allyl intermediates
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A series of C1-symmetrical 1,3-diphosphite ligands with a furanoside backbone have been applied in the Pd-catalysed asymmetric allylic alkylation of mono- and disubstituted linear substrates. These diphosphite ligands were designed by selective
- Gual, Aitor,Castillon, Sergio,Pamies, Oscar,Dieguez, Montserrat,Claver, Carmen
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experimental part
p. 2852 - 2860
(2011/05/14)
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- New 1,2,4,5-tetrakis-(N-imidazoliniummethyl)benzene and 1,2,4,5-tetrakis-(N-benzimidazoliummethyl)benzene salts as N-heterocyclic tetracarbene precursors: synthesis and involvement in ruthenium-catalyzed allylation reactions
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New tetraimidazolinium and tetrabenzimidazolium salts have been prepared. Upon reaction with tBuOK, they generate carbene ligands, which were associated in situ to [RuCp*(MeCN)3]PF6 to produce new ruthenium catalysts that
- Gürbüz, Nevin,Demir, Serpil,?zdemir, Ismail,Cetinkaya, Bekir,Bruneau, Christian
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experimental part
p. 1346 - 1351
(2010/04/02)
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- Modular chiral diphosphite derived from l-tartaric acid. Applications in metal-catalyzed asymmetric reactions
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A new family of C2-symmetric chiral diphosphites was synthesized using two different chiral backbones derived from tartaric acid, combined with chiral binaphthyls or non-chiral substituted biphenyl moieties. Diphosphites were applied to Rh-catalyzed hydroformylation of styrene producing good conversions in mild conditions, fair regioselectivities but low enantioselectivities in all cases. Ligands were also essayed in Pd-catalyzed allylic substitution reactions of linear and cyclic substrates using dimethyl malonate as nucleophile. Conversion rates up to 7200 h-1 were reached, while moderated ee's were attained. In this reaction, a kinetic resolution of rac-1,3-diphenyl-3-acetoxyprop-1-ene was observed, leading to 99% ee of for the unreacted S-substrate and 60% ee of S-alkylated product. Coordination properties of diphosphites in rhodium and palladium complexes related to catalytic species involved in the two previous reactions were investigated. Some ligands form equatorial-equatorial chelates in pentacoordinated complexes [RhH(CO)(PPh3)(diphosphite)], while other act as bridge between two metal atoms. In the catalytic active species [Pd(η3-PhCHCHCHPh)(diphosphite)]PF6 one or two diastereoisomers are formed, depending on the diphosphite structure.
- Rosas-Hernández, Alonso,Vargas-Malvaez, Edgar,Martin, Erika,Crespi, Laura,Bayón, J. Carles
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experimental part
p. 68 - 75
(2010/11/05)
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- Effective chiral ferrocenyl phosphine-thioether ligands in enantioselective palladium-catalyzed allylic alkylations
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Chiral ferrocene-derived phosphine-thioether mixed donor ligands supported by heterocycles effected the palladium-catalyzed enantioselective allylic alkylations with excellent yields and enantioselectivities (up to 96% ee). With cyclic and unsymmetrical a
- Cheung, Hong Yee,Yu, Wing-Yiu,Au-Yeung, Terry T. L.,Zhou, Zhongyuan,Chan, Albert S. C.
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experimental part
p. 1412 - 1422
(2009/12/22)
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- Acyloxylactonisations mediated by lead tetracarboxylates
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The reaction of lead(IV) tetracarboxylates with carboxylic acids containing unsaturated side chains has been found to give acyloxy lactone products in a diastereoselective process; the reaction can be extended to lead(IV) tetrazolates to give the analogous outcome. Mechanistic implications of these results are discussed.
- Cottrell, Ian F.,Cowley, Andrew R.,Croft, Laura J.,Hymns, Lauren,Moloney, Mark G.,Nettleton, Ewan J.,Kirsty Smithies,Thompson, Amber L.
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supporting information; experimental part
p. 2537 - 2550
(2009/08/07)
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- Carbohydrate-Based Pyridine-2-carboxamides for Mo-Catalyzed asymmetric allylic alkylations
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Bis(pyridine-2-carboxamides) were prepared from 1,2-di-amines obtained from α-D-glucose and α-D-mannose. The 11-gands were assessed in molybdenum-catalyzed asymmetric allylic alkylations (AAA) by using both methyl (E)-3-phenyl-2-propenyl and methyl rac-l-
- Del Litto, Raffaella,Benessere, Vincenzo,Ruffo, Francesco,Moberg, Christina
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experimental part
p. 1352 - 1356
(2009/07/26)
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- Novel [ruthenium(substituted-tetramethylcyclopentadiene) (2-quinolinecarboxylato)(allyl)] hexafluorophosphate complexes as efficient catalysts for highly regioselective nucleophilic substitution of aliphatic allylic substrates
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Stable [ruthenium(R-substituted-tetramethylcyclopentadiene)(2- quinolinecarboxylato) (1-R′-substituted-allyl) hexafluorophosphate (R = Me, R′ = H, Me, n-Pr, Ph; R = t-Bu, R′ = Me) and [ruthenium(pentamethylcyclopentadiene)(2-quinolinecarboxylato)(1-n-propylallyl)] tetrafluoroborate (4′a), as allylruthenium(IV) complexes, have been synthesized in one step, starting from [ruthenium(R-substituted- tetramethylcyclopentadiene)tris(acetonitrile) hexafluorophosphate or tetrafluoroborate complexes, quinaldic acid, and allylic alcohols. Single stereoisomers are obtained and the X-ray single crystal structure determinations of 3b (R = t-Bu, R′ = Me) and 4′a allow one to specify the preferred arrangement. Complexes 3a (R = R′ = Me) and 3b are involved as precatalysts favoring the formation of branched products in regioselective nucleophilic allylic substitution reactions, starting from ethyl 2-(E)-hexen-1-yl carbonate and chlorohexene as unsymmetrical aliphatic allylic substrates. Phenols, dimethyl malonate, and primary (aniline) and secondary (pyrrolidine, piperidine) amines have been used as nucleophiles under mild basic conditions. For the first time, the regioselectivity in favor of the branched product obtained from purely aliphatic allylic substrates is close to the high regioselectivity previously reached starting from cinnamyl-type substrates in the presence of ruthenium catalysts.
- Zhang, Hui-Jun,Demerseman, Bernard,Toupet, Loic,Xi, Zhenfeng,Bruneau, Christian
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supporting information; experimental part
p. 1601 - 1609
(2009/07/18)
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- Ruthenium complexes bearing bulky pentasubstituted cyclopentadienyl ligands and evaluation of [Ru(η5-C5Me4R)(MeCN) 3][PF6] precatalysts in nucleophilic allylic substitution reactions
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[Ru(η5-C5Me4R)(MeCN) 3][PF6] (R = CH2 tBu, iPr, tBu, and CF 3; 2-5) complexes were synthesized in two steps starting from the appropriate cyclopentadienes and RuCl3·3H2O. The fully substituted ruthenocenes [Ru(C5Me5)(C 5Me4R*)], [Ru(C5Me5)(C 5nPr4R*)] {R* = (1R,5S)-6,6-dimethylbicyclo- [3.1.1]hept-2-en-2-yl} and [Ru(C5Me5)(C 5nPr5)] were obtained by treating [Ru(C5Me 5)Cl]4 with the corresponding cyclopentadienyllithium salts. Complexes 2-5 were evaluated as catalyst precursors for nucleophilic allylic substitution reactions, and the results were compared to those obtained with the [Ru(C5Me5)(MeCN)3][PF6] (1) precatalyst. The etherification of p-methoxyphenol with the typical aliphatic chlorohexene allylic substrate shows that the introduction of the bulky tert-butyl and trifluoromethyl groups into the tetramethylcyclopentadienyl ring results in a valuable enhancement in regioselectivity in favour of the branched allyl aryl ether. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Zhang, Hui-Jun,Demerseman, Bernard,Xi, Zhenfeng,Bruneau, Christian
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scheme or table
p. 3212 - 3217
(2009/02/07)
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- Iridium-catalyzed asymmetric allylic substitutions-very high regioselectivity and air stability with a catalyst derived from dibenzo[a,e]cyclooctatetraene and a phosphoramidite
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A final tweak: A new phosphoramidite iridium catalyst (see scheme) allows allylic substitutions to be run with a higher degree of regioselectivity than with other iridium catalysts and under aerobic conditions. Mechanistic aspects, in particular, the reversibility of the catalyst formation by C-H activation, are also presented. LL=dibenzocyclooctatetraene.
- Spiess, Stephanie,Welter, Carolin,Franck, Geraldine,Taquet, Jean-Philippe,Helmchen, Guenter
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supporting information; scheme or table
p. 7652 - 7655
(2009/04/11)
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- Benzylic imidazolidinium, 3,4,5,6-tetrahydropyrimidinium and benzimidazolium salts: Applications in ruthenium-catalyzed allylic substitution reactions
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Imidazolidinium, tetrahydropyrimidinium and benzimidazolium salts were prepared. Upon reaction with tBuOK, they generate carbene ligands, which were associated in situ to [RuCp*(MeCN)3]PF6 to produce ruthenium catalysts that are acti
- Yasar, Sedat,Oezdemir, Ismail,Cetinkaya, Bekir,Renaud, Jean-Luc,Bruneau, Christian
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body text
p. 2142 - 2149
(2009/04/04)
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- Features and applications of [Rh(CO)2Cl]2-catalyzed alkylations of unsymmetrical allylic substrates
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(Chemical Equation Presented) A novel regio- and stereoselective [Rh(CO)2Cl]2-catalyzed allylic alkylation of unsymmetrical allylic carbonates was discovered. The regioselectivity of the reaction favors product ratios in which substitution occurs at the carbon bearing the leaving group. When an enantiomerically enriched carbonate (≥99% ee) was examined, the Rh(I)-catalyzed allylic alkylation proceeded stereoselectively to provide the alkylation product with retention of absolute stereochemistry (98% ee). To establish the scope of the [Rh(CO)2Cl]2-catalyzed allylic alkylation, a variety of carbon and heteroatom nucleophiles were examined and the results described. As an application of the Rh(I)-catalyzed allylic alkylation, a series of novel domino reactions have been developed that couple the unique regio- and stereoselective [Rh(CO)2Cl]2- catalyzed alkylation of allylic trifluoroacetates with an intramolecular Pauson-Khand annulation, a cycloisomerization, or a [5+2] cycloaddition. A unique aspect of the method described is the use of a single catalyst to effect sequential transformations in which the catalytic activity is moderated simply by controlling the reaction temperature. Implementation of such processes provides a rapid and efficient entry to a variety of bicyclic carbon skeletons from simple precursors.
- Ashfeld, Brandon L.,Miller, Kenneth A.,Smith, Anna J.,Tran, Kristy,Martin, Stephen F.
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p. 9018 - 9031
(2008/03/13)
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- DIAZAPHOSPHACYCLES
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Diazaphosphacycles comprising compounds having the formula XI : and salts of the compound are provided, wherein the variables W, T, R1, R14, and R15 are as described herein. Transition metal catalysts incorporating such diazaphosphacycles and methods of u
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Page/Page column 79-80
(2008/06/13)
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