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Search for "organolithium reagents" in Full Text gives 29 result(s) in Beilstein Journal of Organic Chemistry.

Efficient synthesis of fluorinated triphenylenes with enhanced arene–perfluoroarene interactions in columnar mesophases

  • Yang Chen,
  • Jiao He,
  • Hang Lin,
  • Hai-Feng Wang,
  • Ping Hu,
  • Bi-Qin Wang,
  • Ke-Qing Zhao and
  • Bertrand Donnio

Beilstein J. Org. Chem. 2024, 20, 3263–3273, doi:10.3762/bjoc.20.270

Graphical Abstract
  • variety of triphenylene derivatives (Figure 1) [44][45][46][47] based on the nucleophilic substitution of various electrophilic perfluoroarenes, including C6F2H4, C6F6, C10F8, and C6F5-Ph, by nucleophilic organolithium reagents. e.g., 2,2’-dilithio-4,4’,5,5’-tetrakis(alkoxy)-1,1’-biphenyls, 2Li-BPn
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Published 16 Dec 2024

gem-Difluorovinyl and trifluorovinyl Michael acceptors in the synthesis of α,β-unsaturated fluorinated and nonfluorinated amides

  • Monika Bilska-Markowska,
  • Marcin Kaźmierczak,
  • Wojciech Jankowski and
  • Marcin Hoffmann

Beilstein J. Org. Chem. 2024, 20, 2946–2953, doi:10.3762/bjoc.20.247

Graphical Abstract
  • using organolithium reagents (Scheme 1), revealing new avenues in fluorinated unsaturated amide synthesis, which are present in numerous natural products, pharmaceuticals, and polymers [34][35][36][37][38]. The obtained α,β-unsaturated amides may represent promising structural motifs for further
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Published 15 Nov 2024

Multicomponent synthesis of α-branched amines using organozinc reagents generated from alkyl bromides

  • Baptiste Leroux,
  • Alexis Beaufils,
  • Federico Banchini,
  • Olivier Jackowski,
  • Alejandro Perez-Luna,
  • Fabrice Chemla,
  • Marc Presset and
  • Erwan Le Gall

Beilstein J. Org. Chem. 2024, 20, 2834–2839, doi:10.3762/bjoc.20.239

Graphical Abstract
  • organolithium reagents, thus limiting functional-group tolerance [11][12][13]. By contrast, heteroleptic (mixed) alkylzinc species (i.e., RZnX) are readily available and can typically be prepared from alkyl halides by direct insertion of metallic zinc into the carbon–halogen bond [14][15][16][17][18][19][20][21
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Published 07 Nov 2024

Beyond n-dopants for organic semiconductors: use of bibenzo[d]imidazoles in UV-promoted dehalogenation reactions of organic halides

  • Kan Tang,
  • Megan R. Brown,
  • Chad Risko,
  • Melissa K. Gish,
  • Garry Rumbles,
  • Phuc H. Pham,
  • Oana R. Luca,
  • Stephen Barlow and
  • Seth R. Marder

Beilstein J. Org. Chem. 2023, 19, 1912–1922, doi:10.3762/bjoc.19.142

Graphical Abstract
  • bibenzyls being the dominant products. These reaction conditions represent an alternative metal-free approach to the conventional synthesis of bibenzyls through the reaction of Grignard or organolithium reagents with benzyl halides, or to the use of highly active metal reagents [33][34][35][36] or metal
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Published 14 Dec 2023

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
  • biomass-derived furfural and 5-methylfurfural, are converted into 3-silylated 2-furyl carbinols upon condensation with organomagnesium or organolithium reagents. The hydroxy unit of the carbinol adducts can be exploited to promote C3(sp2)–Si bond functionalization through intramolecular activation. Two
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Published 16 Sep 2022

Synthesis of novel alkynyl imidazopyridinyl selenides: copper-catalyzed tandem selenation of selenium with 2-arylimidazo[1,2-a]pyridines and terminal alkynes

  • Mio Matsumura,
  • Kaho Tsukada,
  • Kiwa Sugimoto,
  • Yuki Murata and
  • Shuji Yasuike

Beilstein J. Org. Chem. 2022, 18, 863–871, doi:10.3762/bjoc.18.87

Graphical Abstract
  • inexpensive and easy to handle Se powder as the Se source. The reaction proceeded with terminal alkynes having various substitutions, such as aryl, vinyl, and alkyl groups. The obtained alkynyl imidazopyridinyl selenide was found to undergo nucleophilic substitution reaction on Se atom using organolithium
  • reagents and 1,3-dipolar azide–alkyne cycloaddition based on the alkyne moiety. Keywords: alkynyl imidazopyridinyl selenide; copper catalyst; imidazo[1,2-a]pyridine; selenium; tandem reaction; terminal alkyne; Introduction Imidazo[1,2-a]pyridines are important heterocycles that serve as key functional
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Published 19 Jul 2022

A sustainable strategy for the straightforward preparation of 2H-azirines and highly functionalized NH-aziridines from vinyl azides using a single solvent flow-batch approach

  • Michael Andresini,
  • Leonardo Degannaro and
  • Renzo Luisi

Beilstein J. Org. Chem. 2021, 17, 203–209, doi:10.3762/bjoc.17.20

Graphical Abstract
  • to access aziridines with great structural variability [21]. The reaction of azirines with Grignard and organolithium reagents has been poorly investigated, and only without using green and renewable solvents [22][23]. In turn, 2H-azirines can be smoothly obtained through intramolecular cyclization
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Published 20 Jan 2021

Oxime radicals: generation, properties and application in organic synthesis

  • Igor B. Krylov,
  • Stanislav A. Paveliev,
  • Alexander S. Budnikov and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2020, 16, 1234–1276, doi:10.3762/bjoc.16.107

Graphical Abstract
  • organolithium reagents 41 at 0 °C in Et2O forming mainly di-tert-butyl oxime 1f and the products of C–O coupling [86]. The reactions were performed by addition of the solution of the organometallic compound 41 in Et2O to the solution of di-tert-butyliminoxyl radical in Et2O. The product yields obtained
  • employing organolithium reagents are presented below (Scheme 14). The Grignard reagents demonstrated very similar results that are omitted. Among the major C–O coupling product (oxime ether 42) small amounts of C–N coupling products (nitrones 43) were detected in the case of sterically unhindered
  • organolithium reagents. Presumably, the reaction proceeds via SET from the organometallic compound and iminoxyl radical with the formation of an oxime anion and an intermediate C-centered radical. In the case of MeLi and PhLi, which correspond to the most reactive methyl and phenyl radicals, products 44 of
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Published 05 Jun 2020

Copper-catalysed alkylation of heterocyclic acceptors with organometallic reagents

  • Yafei Guo and
  • Syuzanna R. Harutyunyan

Beilstein J. Org. Chem. 2020, 16, 1006–1021, doi:10.3762/bjoc.16.90

Graphical Abstract
  • co-workers elaborated the copper-catalysed ring opening reaction of oxabicyclic alkene substrates using organolithium reagents, finding excellent anti selectivities and enantioselectivity (Scheme 12) [42]. During the optimisation studies, they discovered that when the Lewis acid BF3·OEt2 was employed
  • oxabicyclic substrates with organolithium reagents (selected examples). Copper-catalysed ring opening of polycyclic meso hydrazines. Copper-catalysed ACA of Grignard reagents to alkenyl-substituted aromatic N-heterocycles. Copper-catalysed ACA of Grignard reagents to β-substituted alkenylpyridines. Copper
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Published 14 May 2020

Synthesis of six-membered silacycles by borane-catalyzed double sila-Friedel–Crafts reaction

  • Yafang Dong,
  • Masahiko Sakai,
  • Kazuto Fuji,
  • Kohei Sekine and
  • Yoichiro Kuninobu

Beilstein J. Org. Chem. 2020, 16, 409–414, doi:10.3762/bjoc.16.39

Graphical Abstract
  • in terms of the functional group tolerance and versatility of these previously reported synthetic methods due to the use of a stoichiometric amount of the organolithium reagents. In addition, despite these contributions, catalytic reaction systems have not been developed as much [26][27]. The sila
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Published 17 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

Graphical Abstract
  • where the metalated organohalogen compound is reacted with the halogen phosphine. Alternatively, the metal phosphide can be reacted with an organohalogen compound leading to the desired product. The most commonly used trans-metalation reagents are Grignard [54] or organolithium reagents [55] and other
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Published 12 Mar 2020

Efficient synthesis of pyrazolopyridines containing a chromane backbone through domino reaction

  • Razieh Navari,
  • Saeed Balalaie,
  • Saber Mehrparvar,
  • Fatemeh Darvish,
  • Frank Rominger,
  • Fatima Hamdan and
  • Sattar Mirzaie

Beilstein J. Org. Chem. 2019, 15, 874–880, doi:10.3762/bjoc.15.85

Graphical Abstract
  • products 5a–d were not formed. The reaction mechanism is shown in Scheme 2. The chemical structures of the products 5a–d are shown in Figure 4. Usually, to activate the nitrile group for cyclization reaction, the existence of Lewis acid, the addition of organolithium reagents or metal
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Published 11 Apr 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

Graphical Abstract
  • 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

Recent progress in the racemic and enantioselective synthesis of monofluoroalkene-based dipeptide isosteres

  • Myriam Drouin and
  • Jean-François Paquin

Beilstein J. Org. Chem. 2017, 13, 2637–2658, doi:10.3762/bjoc.13.262

Graphical Abstract
  • ester gave the corresponding aldehyde 45 which was then transformed into the α-fluoroenimine 47. This was selectively converted into the corresponding sulfinylamines using Grignard reagents to access (S)-amino acids 48, while addition of organolithium reagents gave (R)-amino acids. A sequence of N- and
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Published 12 Dec 2017

Conjugated nitrosoalkenes as Michael acceptors in carbon–carbon bond forming reactions: a review and perspective

  • Yaroslav D. Boyko,
  • Valentin S. Dorokhov,
  • Alexey Yu. Sukhorukov and
  • Sema L. Ioffe

Beilstein J. Org. Chem. 2017, 13, 2214–2234, doi:10.3762/bjoc.13.220

Graphical Abstract
  • other nitrosoalkene sources (see Scheme 1) in reaction with organometallic compounds is very limited. Thus, Seebach and co-authors reported the addition of organolithium reagents to O-silyl nitronates 58 leading to α-substituted oximes 59 (Scheme 20) [42]. It is likely, that upon treatment with
  • (+/−)-perhydrohistrionicotoxin. Addition of Gilman’s reagents to α,β-epoxy oximes 53. Addition of Gilman’s reagents to α-chlorooximes. Reaction of silyl nitronate 58 with organolithium reagents via nitrosoalkene NSA12. Reaction of β-ketoxime sulfones 61 and 63 with lithium acetylides. Electrophilic addition of nitrosoalkenes
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Published 23 Oct 2017

Contribution of microreactor technology and flow chemistry to the development of green and sustainable synthesis

  • Flavio Fanelli,
  • Giovanna Parisi,
  • Leonardo Degennaro and
  • Renzo Luisi

Beilstein J. Org. Chem. 2017, 13, 520–542, doi:10.3762/bjoc.13.51

Graphical Abstract
  • example on the use of microreactor technology for the development of sustainable chemical processes, is represented by the direct introduction of the tert-butoxycarbonyl group into organometallic reagents [34]. The reaction between organolithium reagents and di-tert-butyl dicarbonate run under flow
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Published 14 Mar 2017

β-Amino functionalization of cinnamic Weinreb amides in ionic liquid

  • Yi-Ning Wang,
  • Guo-Xiang Sun and
  • Gang Qi

Beilstein J. Org. Chem. 2016, 12, 2372–2377, doi:10.3762/bjoc.12.231

Graphical Abstract
  • , Grignard and organolithium reagents or ester enolates, the Weinreb amides can be easily converted into aldehydes, ketones, and β-keto esters, respectively [13][14][15][16][17][18][19][20]. Therefore, the transformation of β-amino Weinreb amides can provide a promising pathway towards the achievement of β
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Published 11 Nov 2016

Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines

  • David R. Chisholm,
  • Garr-Layy Zhou,
  • Ehmke Pohl,
  • Roy Valentine and
  • Andrew Whiting

Beilstein J. Org. Chem. 2016, 12, 1851–1862, doi:10.3762/bjoc.12.174

Graphical Abstract
  • literature, however, to our knowledge this is the only such reaction reported with an aromatic amide [31]. Organolithium reagents have been used to synthesise the analogous alkylated DHQ compounds [27]. Compounds 21 and 22 were found to undergo slow degradation (over 2–4 weeks), as indicated by the
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Published 16 Aug 2016

Preparation of phosphines through C–P bond formation

  • Iris Wauters,
  • Wouter Debrouwer and
  • Christian V. Stevens

Beilstein J. Org. Chem. 2014, 10, 1064–1096, doi:10.3762/bjoc.10.106

Graphical Abstract
  • of different starting oxazaphospholidine borane complexes 7 from (−)-ephedrine or (+)-ephedrine [38] or by starting from the same oxazaphospholidine borane adduct 7 and then changing the order of addition of the organolithium reagents (Scheme 2). Acidolysis with HCl of compounds 8a results in the
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Published 09 May 2014

Synthesis of novel derivatives of 5-hydroxymethylcytosine and 5-formylcytosine as tools for epigenetics

  • Anna Chentsova,
  • Era Kapourani and
  • Athanassios Giannis

Beilstein J. Org. Chem. 2014, 10, 7–11, doi:10.3762/bjoc.10.2

Graphical Abstract
  • treatment with various Grignard reagents (methylmagnesium bromide, THF, 0 °C → room temperature, or vinylmagnesium bromide, THF, 0 °C → room temperature) and organolithium reagents (lithium (trimethylsilyl)acetylide, THF, −40 °C → −20 °C or lithium phenylacetylide, THF, −78 °C → −50 °C) (Scheme 2). These
  • treatment of aldehyde 1 with β,β,β-trichloro-tert-butoxycarbonyl chloride (TCBocCl) [31] in the presence of pyridine in DCM (Scheme 3). The reaction of 4 with Grignard (methylmagnesium bromide, THF, 0 °C → room temperature, or vinylmagnesium bromide, THF, 0 °C → room temperature) and organolithium reagents
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Published 03 Jan 2014

Ring-opening reaction of 2,5-dioctyldithieno[2,3-b:3',2'-d]thiophene in the presence of aryllithium reagents

  • Hao Zhong,
  • Jianwu Shi,
  • Jianxun Kang,
  • Shaomin Wang,
  • Xinming Liu and
  • Hua Wang

Beilstein J. Org. Chem. 2013, 9, 767–774, doi:10.3762/bjoc.9.87

Graphical Abstract
  • . To construct DTT functional materials, deprotonation of DTT with organolithium reagents seems to be one of the most important approaches. However, the ring-opening reaction of DTT leading to the cleavage of the center ring can be observed in the presence of n-BuLi. In our previous work, we reported
  • , high selectivity towards the ring opening was observed with n-BuLi when compared with other organolithium reagents. However, most of these ring-opening reactions mentioned above take place by using n-BuLi as the nucleophile to attack the sulfur atoms of thiophenes. Other organolithium reagents have
  • rarely been employed for this kind of reaction. Furthermore, the relationship between the nucleophilicity of organolithium reagents and the efficiency of the ring opening of fused thiophenes has not been discussed. In this paper, we present the ring opening of 2,5-dioctyldithieno[2,3-b:3',2'-d]thiophene
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Published 19 Apr 2013

Carbolithiation of N-alkenyl ureas and N-alkenyl carbamates

  • Julien Lefranc,
  • Alberto Minassi and
  • Jonathan Clayden

Beilstein J. Org. Chem. 2013, 9, 628–632, doi:10.3762/bjoc.9.70

Graphical Abstract
  • primary, secondary and tertiary organolithium reagents. N-tert-butoxycarbonyl vinylcarbamates may be carbolithiated, protonated and deprotected in a one-pot synthesis of amines employing this unusual umpolung nucleophilic β-alkylation. With β-substituted vinylureas, the carbolithiation is
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Published 28 Mar 2013

Synthesis of SF5-containing benzisoxazoles, quinolines, and quinazolines by the Davis reaction of nitro-(pentafluorosulfanyl)benzenes

  • Petr Beier and
  • Tereza Pastýříková

Beilstein J. Org. Chem. 2013, 9, 411–416, doi:10.3762/bjoc.9.43

Graphical Abstract
  • [26] nucleophiles, and oxidative nucleophilic substitution of hydrogen (ONSH) with Grignard and organolithium reagents [27]. This chemistry significantly expanded the range of available SF5-benzene derivatives. The synthetic chemistry and biological activity of pentafluorosulfanyl organic molecules
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Published 21 Feb 2013

Intramolecular carbolithiation of N-allyl-ynamides: an efficient entry to 1,4-dihydropyridines and pyridines – application to a formal synthesis of sarizotan

  • Wafa Gati,
  • Mohamed M. Rammah,
  • Mohamed B. Rammah and
  • Gwilherm Evano

Beilstein J. Org. Chem. 2012, 8, 2214–2222, doi:10.3762/bjoc.8.250

Graphical Abstract
  • formal synthesis of the anti-dyskinesia agent sarizotan, further extends the use of ynamides in organic synthesis and further demonstrates the synthetic efficiency of carbometallation reactions. Keywords: carbolithiation; carbometallation; dihydropyridines; organolithium reagents; pyridines; sarizotan
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Published 21 Dec 2012

Directed ortho,ortho'-dimetalation of hydrobenzoin: Rapid access to hydrobenzoin derivatives useful for asymmetric synthesis

  • Inhee Cho,
  • Labros Meimetis,
  • Lee Belding,
  • Michael J. Katz,
  • Travis Dudding and
  • Robert Britton

Beilstein J. Org. Chem. 2011, 7, 1315–1322, doi:10.3762/bjoc.7.154

Graphical Abstract
  • addition of organolithium reagents to arene tricarbonylchromium complexes [7] and α,β-unsaturated aldimines [8]. Notably, derivatives of hydrobenzoin in which the aromatic rings have been functionalized in the ortho and ortho' positions often display improved diastereo- or enantioselectivity over the
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Published 22 Sep 2011
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