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#1Are n-BuLi/TMEDA-Mediated Arene Ortholithiations Directed ...
n-BuLi/TMEDA in hydrocarbons has been shown to be dimer 12; 36 [n-BuLi] refers to the concentration of monomer subunit (normality). [TMEDA] ...
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#3REACTIONS OF CHELATED ORGANOLITHIUM ...
(TMEDA) forms a five-membered ring chelate with butyllithium (I) which is ... reactivity of the BuLi-TMEDA complex for metalation can be illustrated.
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#4Are n-BuLi/TMEDA-Mediated Arene ... - Collum Group
so-called complex-induced proximity effect (CIPE).5 While the ... for lithiation by n-BuLi/TMEDA.20 These examples underscore several key questions:.
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#5Directed Metalation: A Survival Guide
complex -induced proximity effect (CIPE) and at the same time be poorly ... n-BuLi, TMEDA ... MeLi, n-BuLi, sec-BuLi and t-BuLi are the most common.
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#6Dalton Trans. - RSC Publishing - The Royal Society of Chemistry
由 A Hildebrand 著作 · 2006 · 被引用 15 次 — Co-complexes of ortho-dilithiated thiophenol or ... Deprotonation of the TMEDA molecule with nBuLi was also observed in n-hexane at 50 °C.
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#7Half-Lives of Organolithium Reagents in Common Ethereal ...
of frequently used lithiation reagents (n-, s-, or t-BuLi ... complex ether2. 8.05 h. 1.02 h kinetics s-BuLi/TMEDA stab. at ether. 0.5c0 s-BuLi. 1187 min.
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#8N BuLi | Sigma-Aldrich
Aggregation studies of complexes containing a chiral lithium amide and n-Butyllithium. Deyu Li et al. The Journal of organic chemistry, 73(6) ...
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#9ortho metalation
sec-BuLi, TMEDA. 2. Me3SnCl. SnMe3. OCONEt2. OCONEt2. The highly hindered amide base TMPMgCl•LiCl has been shown to effect efficient directed metallation ...
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#102001, Vol.30, No.7 - CSJ Journals
Aromatization of highly alkyl-substituted dihydroanthracene was performed with the n-BuLi/TMEDA/MeI. Treatment of 1,2,3,4,5,6,7,8-octapropyl-9 ...
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#11Are n-BuLi/TMEDA-Mediated Arene ... - ResearchGate
Download Citation | Are n-BuLi/TMEDA-Mediated Arene ... with the lone pairs of the heteroatom forming a prelithiation complex (PLC).
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#12Role of Organolithium Aggregates and Mixed Aggregates in ...
toluene solvent by a n-BuLi−alkoxide superbase.23 ... CH2Li·TMEDA forms a complex ladder in which all three basic.
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#13Structure of n-butyllithium in mixtures of ethers and diamines
n-BuLi in diamine/dialkyl ether mixtures forms ensembles of hetero- and homosolvated dimers. Solutions in TMEDA/THF (TMEDA = N,N,N' ...
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#14I [I IQ I - Nature
and absence of N,N,N',N'-tetramethylethylenediamine (TMEDA). ... distilled over CaH2 • s-BuLi, TMEDA, and ... various types of complicated rings can be.
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#15Is N,N,N,N-Tetramethylethylenediamine a Good Ligand for
observable anisole-n-BuLi complex in hydrocarbon solution fails to undergo ortho metalation.% Addition of TMEDA causes the quantitative displacement of.
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#16organolithium reagents 1
Treatment of benzene with n-BuLi leads to little or no reaction, whereas addition of. TMEDA leads to quantitative lithiation. Alkyllithium reagents combined ...
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#17troticene lithiation and platinum-catalyzed hydrosilylation
increased reactivity of the n-butyllithium/TMEDA complex relative to the uncomplexed ... t-BuLi ortho- lithiation peri- lithiation n-BuLi or n-BuLi/TMEDA.
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#18Tetramethylethylenediamine - wikidoc
In such complexes, the TMEDA serves as a bidentate ligand. ... BuLi/TMEDA is able to metallate or even doubly metalate many substrates ...
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#19US3769345A - Method of preparing organolithium amine ...
ORGANOLITHIUM AMINE COMPLEXES ARE PREPARED BY ADMIXING AN ORGANOLITHIUM, ... Therefore, the BuLi-TMEDA-benzene solution consisted solely of phenyllithium ...
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#20directed metallationx
Benzylic lithiation is usually done by switching to a lithium amide base. This can be used to advantage in many cases. CONEt2. 1) s-BuLi, TMEDA. THF, ...
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#21"High" Temperature Lithiation-trapping of Nitrogen and ...
BuLi /TMEDA complex can occur when the temperature is above 0 °C (entry 7). A number of studies concerning the cleavage of cyclic ethers by organolithium ...
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#22Prof. Dr. Thomas Lindel
Addition of TMEDA enables deprotonation of PhH by n-BuLi by changing the cluster ... The (n-BuLi-TMEDA)2 complex ... was ... pure TMEDA added via syringe.
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#23United States Patent Office
at 25° C. Since the benzyllithium-TMEDA complex ... BuLi-TMEDA in 8 ml. n-heptane at 50-60° C. for three hours. Vacuum drying the total mixture gave an ...
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#24enantioselective lithiation - Macmillan Group
BuLi. Ph. Me. N(iPr)2. O s-BuLi/TMEDA ... complex, C, with a large equilibrium constant, Kc ... resolve the diastereomeric complexes.
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#25Twofold Ferrocene C–H Lithiations For One-Step Difunctionaliza
Unlike butyllithium, the butyllithium–TMEDA chelate (2.0 ... 1) BuLi–TMEDA ... complexes for asymmetric catalysis, the study was extend-.
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#26Organometallic Chemistry
aggregates of 2, 3 or 4 molecules, and of complexes with solvent if ethers are used ... TMEDA or HMPA deoligomerize hexameric n-BuLi in hexane.
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#27Certain applications of heteroatom ... - Semantic Scholar
TMEDA has recently been reported.4 Owing to its insufficient bulk, n-BuLi, although used in ... chlorobenzamide resulted in a complex mixture.
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#28On the Mechanism of the Ortho-Directed Metalation of Anisole ...
alkyllithiums with the DMG (“complex induced proximity ... s-BuLi/TMEDA proceeds through the prior formation of an alkyllithium-urea complex ...
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#29搜索
6Li and (13)C NMR spectroscopic studies were carried out on [(6)Li]n-BuLi and ... solvation on the structures and reactivities of RLi-diamine complexes: 1 ...
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#30Stoichiometric Metallation Reactions
NB. use of 2 equiv of t-BuLi common. ... TMEDA co-solvent. – review (structures of lithium complexes): van Koten Angew. Chem. int. ... 1) s-BuLi/TMEDA.
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#31Chelation-Assisted Substrate-Controlled Asymmetric Lithiation ...
... with high lk-diastereoselectivity: the bicyclic chelate complexes 3a and 3b ... by s-BuLi/TMEDA in diethylether to form an α-lithiated species [1,2], ...
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#32Complex-Induced Proximity Effect in Lithiation - Bentham Open
α–lithiation of TMEDA in the presence of t-BuLi was reported to give, after electrophilic quenching, a tridentate.
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#33TMEDA - Big Chemical Encyclopedia
A 4 1 n-BuLi TMEDA complex is a tetramer accommodating two TMEDA molecules, which, rather than chelating a lithium, link the tetrameric units.
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#34Reactions of 1,2-Diphosphetenes with Lithium ... - EPA - HERO
... and t-BuLi cleave the P-P bond of 1,2,3,4-tetraphenyldiphosphetene in hexane whereas it is necessary to use the t-BuLi-TMEDA complex in ...
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#35Smith Review As Submitted.pdf - -ORCA - Cardiff University
a complex 4 with the Lewis acidic organolithium reagent and direct the ... while in the presence of TMEDA or DABCO, where the n-BuLi exists as either a ...
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#36Directed lithiation of simple aromatics and heterocycles for ...
n-BuLi cyclohexane/TMEDA a. 0 to 25. 103,104. SH n-BuLi. TMEDA ... ortho-substituted derivatives that might be difficult to prepare by other means.
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#37Organic Syntheses Procedure
... which becomes warm as the organolithium-diamine complex forms, ... Tertiary amines such as N,N,N',N'-tetramethylethylenediamine (TMEDA) and 1 ...
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#38THE REGIOSPECIFIC LITHIATION OF AROMATIC ACETALS
Acetals 9-11 are only deprotonated with _t^-BuLi and even then products are only ... t-BuLi n-BuLi, n-BuLi-TMEDA t-BuLi n-BuLi t-BuLi n-BuLi, n-BuLi-TMEDA.
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#392.2: Organometallic Compounds of Alkali Metals (Sodium and ...
Addition of TMEDA may break down the aggregates of lithium alkyls to give lower nuclearity complexes. E.g. [ nBuLi.TMEDA]2
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#40Regiodivergent enantioselective CH functionalization of Boc-1 ...
The lithiation of compound 7a with the achiral s-BuLi•TMEDA complex, followed by transmetallation with ZnCl2 and cross-coupling with bromobenzene in the ...
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#41The synthesis and structure of a thiobenzyl-functionalized ...
Deprotonation with BuLi/TMEDA in THF and the addition of FeCl2 gave the expected 1 ... and structure of a thiobenzyl-functionalized dibenzoferrocene complex.
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#42Certain applications of heteroatom ... - quod.lib.umich.edu.
E1. sec-BuLi/TMEDA/THF/-78 CCONEt2OE Scheme 2 ... of the thioindoxyl (3) synthesized from N,N-diethyl-2- chlorobenzamide resulted in a complex mixture.
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#43directed ortho metalation – boronation suzuki-miyaura cross ...
complex, 1.18 is on the path of the reaction prior to α-lithiation 1.19 thus ... lithiation of 1.48 using s-BuLi·TMEDA occurs ortho to the diisopropyl ...
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#44Unravelling Factors Affecting Directed Lithiation of ... - CORE
a complex 4 with the Lewis acidic organolithium reagent and direct the ... while in the presence of TMEDA or DABCO, where the n-BuLi exists as either a ...
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#45Are n-BuLi/TMEDA-Mediated Arene Ortholithiations ... - glocat
Are n-BuLi/TMEDA-Mediated Arene Ortholithiations Directed? Substituent-Dependent Rates, Substituent-Independent Mechanisms-article.
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#46Facile Synthesis of β,β-Difluorostyrenes via the Negishi ...
of Thermally Stable 2,2-Difluorovinyl Zinc–TMEDA Complex ... s-BuLi was added to the mixture of 1 and TMEDA, followed by.
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#47Factors influencing prenylation of an aromatic organolithium
of TMEDA to the ether solution of 6 and n-BuLi resulted in an increase in the proportion ... metal proton exchange.13, 17-19 The resulting complex includes.
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#48Directed ortho metalation reactions. Convergent synthesis of ...
generated anionic 1-tetra101 chromium tricarbonyl complex ... a: 2 equiv. n- BuLi/TMEDA/EtzO/reflux; 14/Et20/ - 45°C; b: TsOH/Tol/reflux (77% overall); c: ...
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#49The directed ortho metalation reaction. Methodology ... - IUPAC
Conditions. Yield. %. OMOM. 1-BULi / HMPA' / THF 1-78OC. OCONEt2 s-BULi I TMEDA / THF I-78'C. OSEM. ' Omitted for E = TMS n-BuLi / Et20 / RT.
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#50Taming Highly Reactive Species for Use in Organic Synthesis
Figure 9: Crystal structures of Schlosser's base complexes during ... the increased metalating power of the n-BuLi/TMEDA complex resulted primarily from.
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#51Kinetic and thermodynamic stability of lithio anions in the ...
Thermodynamic deprotonation with BuLi ... In this system, the Bu s Li/TMEDA complex at -78 o C effects ortho metalation preferentially while LDA at 0 o C ...
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#52REPORT DOCUMENTATION PAGE K
It is believed that the reactive species is a complex in which the ... 1:2:6:8 for PMS:t-BuLi:t-PeOK:TMEDA and the reaction product was ...
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#53Texas A&M University Libraries - Scholars
Reaction of the cyanomethyl rhenium complex (.eta.5-C5H5)Re(NO)(PPh3)(CH2CN) with n-BuLi/TMEDA; generation, stereospecific alkylation, and basicity of a ...
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#54Lithiated oxazolinyloxiranes and oxazolinylaziridines - De ...
Subjected to lithiation (s-BuLi/TMEDA, THF, –100 °C) diphenyloxirane 1 generates ... monomers, namely (R)-η3-12-Li and (S)-η3-12-Li, mediated by a complex ...
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#55Advanced Organic Chemistry: Part A: Structure and Mechanisms
A 4:1 n-BuLi:TMEDA complex is a tetramer accommodating two TMEDA molecules, which, rather than chelating a lithium, links the tetrameric units.
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#561985 - Chinese J. Polym. Sci
In n-BuLi-TMEDA-butadiene system, Hay[4) determined Ean to be 3.47 kcal/mol. ... complex formed from the polymer lithium active chain and TMEDA is stable, ...
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#57Use of Organometallic Intermediates in Organic Synthesis
2- and 4-Substituted Pyridines: Synthesis of More Complex ... presence of TMEDA or DABCO, where the n-BuLi exists as either a dimer or.
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#58Homologation of Boronic Esters with Lithiated Epoxides for the ...
synthesis.5 Thus, we hoped that following ate complex formation (1) and 1,2-metalate ... oxide with s-BuLi-TMEDA at -98 °C, followed by addition.
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#59and β3-amino acids - edoc
Then, lithiating compound. 7b-D with the achiral s-BuLi•TMEDA complex and perform- ing the C4-selective arylation under the same conditions as above furnished ...
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#60Isomers of Alkali Metal (Methylbenzyl)allylamides - Monash ...
potassium complexes. Addition of (S)-N-(α-methylbenzyl)- methallylamine to a 1:1 mixture of n-BuLi and PMDETA or. TMEDA in hexane yielded a ...
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#61NEW STRATEGIES FOR THE PERI LITHIATION - CiteSeerX
provide a powerful regiospecific method for functionalizing complex aromatic rings. Presently, directed ortho metalations are ... s-BuLi, TMEDA, THF, -78.
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#62Advances in Organometallic Chemistry - 第 64 頁 - Google 圖書結果
(22) concluded from their kinetics studies that the active species initially is a complex (5) between the t-BuLi and the TMEDA and that, in the presence of ...
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#63Metalation of Azines and Diazines - 第 104 頁 - Google 圖書結果
Using BuLi·TMEDA chelate as the metalating agent affords the ... similarly observed when 4-pivaloyl-aminoquinoline is treated with BuLi·TMEDA complex at À50 ...
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#64NASA Tech Brief - 第 71-10210 頁 - Google 圖書結果
TMEDA complex as an initiator for polymerization was demonstrated by adding ... with the following sequence of reactions : ( 1 ) BuLi + TMEDA - BuLi.
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#65NASA Tech Brief - Google 圖書結果
TMEDA complex as an initiator for polymerization was demonstrated by adding ... by reacting butyllithium ( BuLi ) and an excess of TMEDA in an inert solvent ...
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#66Handbook of Reagents for Organic Synthesis: Reagents for ...
Compared to the analogous n-BuLi/TMEDA complex, s-BuLi/TMEDA is considerably more potent as a metalating agent; e.g. the lithiation of Me4Si proceeds ∼1000 ...
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#67Question: 1) n-BuLi, TMEDA 2) B(OMe)3 NEt2 3) H3O+ - Chegg
Answer to Solved 1) n-BuLi, TMEDA 2) B(OMe)3 NEt2 3) H3O+.
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