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Search for "trifluoromethylation" in Full Text gives 66 result(s) in Beilstein Journal of Organic Chemistry.

Visible-light-induced radical cascade cyclization: a catalyst-free synthetic approach to trifluoromethylated heterocycles

  • Chuan Yang,
  • Wei Shi,
  • Jian Tian,
  • Lin Guo,
  • Yating Zhao and
  • Wujiong Xia

Beilstein J. Org. Chem. 2024, 20, 118–124, doi:10.3762/bjoc.20.12

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  • enables a rapid access to heterocycles containing a trifluoromethyl group. Keywords: cascade reaction; indole derivatives; photocatalysis; radical chain process; trifluoromethylation; Introduction Dihydropyrido[1,2-a]indolone (DHPI) skeletons are commonly found in natural products and pharmaceutical
  • trifluoromethyl radical source under light irradiation. Umemoto’s reagent, which is capable of releasing a trifluoromethyl radical via a photoinduced single-electron-transfer (SET) process, is usually employed to enable the trifluoromethylation of unsaturated substrates [25][26][27]. Herein, we report a protocol
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Published 19 Jan 2024

Recent advancements in iodide/phosphine-mediated photoredox radical reactions

  • Tinglan Liu,
  • Yu Zhou,
  • Junhong Tang and
  • Chengming Wang

Beilstein J. Org. Chem. 2023, 19, 1785–1803, doi:10.3762/bjoc.19.131

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  • provided a more sustainable and economically viable approach but also demonstrated excellent performance in various transformations. It had been successfully applied to a series of radical reactions, including trifluoromethylation, deaminative alkylation, and asymmetric versions of Minisci reactions
  • urgent need to develop diverse monofluoromethylation methods. In this context, Chen and his colleagues recently developed a concise photocatalytic procedure for achieving monofluoromethylation, as well as di- and trifluoromethylation of various alkenes (Scheme 25) [50]. The synthetic method also
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Published 22 Nov 2023

Trifluoromethylated hydrazones and acylhydrazones as potent nitrogen-containing fluorinated building blocks

  • Zhang Dongxu

Beilstein J. Org. Chem. 2023, 19, 1741–1754, doi:10.3762/bjoc.19.127

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  • . Keywords: acylhydrazones; difluoromethylation; dihydropyridazine; fluorinated building blocks; hydrazones; imidazolidines; pyrazoles; pyrazolidines; pyrazolines; trifluoromethylation; Introduction The introduction of fluorine into pharmaceuticals, agrochemicals, and materials can significantly enhance
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Published 15 Nov 2023

Transition-metal-catalyzed C–H bond activation as a sustainable strategy for the synthesis of fluorinated molecules: an overview

  • Louis Monsigny,
  • Floriane Doche and
  • Tatiana Besset

Beilstein J. Org. Chem. 2023, 19, 448–473, doi:10.3762/bjoc.19.35

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  • compounds by transition-metal-catalyzed C–H bond activation. This review focused on the construction of C(sp2)–XRF bonds and C(sp3)–XRF bonds with an emphasis on the trifluoromethylation reaction and transformations using emergent fluorinated residues (SCF3, SeCF3, SCF2H, SCF2CO2Et or OCH2CF3 groups). Well
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Published 17 Apr 2023

Synthesis of α-(perfluoroalkylsulfonyl)propiophenones: a new set of reagents for the light-mediated perfluoroalkylation of aromatics

  • Durbis J. Castillo-Pazos,
  • Juan D. Lasso and
  • Chao-Jun Li

Beilstein J. Org. Chem. 2022, 18, 788–795, doi:10.3762/bjoc.18.79

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  • of aromatics, for which trifluoromethylation was also possible in good to high yields for electron-rich aromatic rings [10]. In this protocol, inspired by Norrish type I reactions and the elimination of β-substituents after ketone photoexcitation [11][12][13], a series of reagents containing an α
  • of these reagents as late-stage functionalization agents [26][27]. For a trend in reactivity, a more comprehensive scope of arenes and heteroarenes has been explored with the innate trifluoromethylation methodology previously reported by our group [10]. Conclusion In summary, we have successfully
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Published 04 Jul 2022

Iron-catalyzed domino coupling reactions of π-systems

  • Austin Pounder and
  • William Tam

Beilstein J. Org. Chem. 2021, 17, 2848–2893, doi:10.3762/bjoc.17.196

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  • alkyl radical. Perchlorinated species 139a, like the substrates investigated by Li and Shen, most likely undergo thermal homolytic bond cleavage and do not rely on a radical initiator. In 2016, Shi and co-workers investigated the trifluoromethylation cascade of acrylamide-tethered
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Published 07 Dec 2021

Recent advances in the tandem annulation of 1,3-enynes to functionalized pyridine and pyrrole derivatives

  • Yi Liu,
  • Puying Luo,
  • Yang Fu,
  • Tianxin Hao,
  • Xuan Liu,
  • Qiuping Ding and
  • Yiyuan Peng

Beilstein J. Org. Chem. 2021, 17, 2462–2476, doi:10.3762/bjoc.17.163

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  • structural motifs to provide the functionalized pyridine and pyrrole derivatives. The functionalization reactions cover iodination, bromination, trifluoromethylation, azidation, carbonylation, arylation, alkylation, selenylation, sulfenylation, amidation, esterification, and hydroxylation. We also briefly
  • functionalizations of pyrrole derivatives, such as iodination, bromination, trifluoromethylation, azidation, carbonylation, arylation, and alkylation. The proposed mechanism generally involves two kinds of intramolecular cyclizations: one is 6-endo-dig cyclization to promote the formation of pyridine ring
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Published 22 Sep 2021

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

  • Renato L. Carvalho,
  • Amanda S. de Miranda,
  • Mateus P. Nunes,
  • Roberto S. Gomes,
  • Guilherme A. M. Jardim and
  • Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126

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Published 30 Jul 2021

Synthetic reactions driven by electron-donor–acceptor (EDA) complexes

  • Zhonglie Yang,
  • Yutong Liu,
  • Kun Cao,
  • Xiaobin Zhang,
  • Hezhong Jiang and
  • Jiahong Li

Beilstein J. Org. Chem. 2021, 17, 771–799, doi:10.3762/bjoc.17.67

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  • conditions, more attention has been paid to this efficient strategy for C–C-bond formation. In 2015, Yu and colleagues [27] proposed a method for direct C–H trifluoromethylation of aromatic hydrocarbons through an EDA complex. Trifluoromethylated product 61 was synthesized by employing tryptamine derivative
  • corresponding hydrotrifluoromethylation products with moderate to good yield. In 2017, Yu and colleagues [30] proposed an EDA-complex-induced alkyne trifluoromethylation reaction. The EDA complex formed by a catalytic quantity of Togni reagent 69 and NMM initiated the chain propagation, causing the final alkyne
  • trifluoromethylation (Scheme 25). A variety of olefins, such as ene carbamates, styrene, aliphatic olefins, vinyl ethers, and acrylates are compatible in this approach, affording corresponding β-(trifluoromethyl)alkynes with good to excellent yield. The bifunctionalization was achieved by an EDA-complex-initiated
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Published 06 Apr 2021

Metal-free visible-light-enabled vicinal trifluoromethyl dithiolation of unactivated alkenes

  • Xiaojuan Li,
  • Qiang Zhang,
  • Weigang Zhang,
  • Jinzhu Ma,
  • Yi Wang and
  • Yi Pan

Beilstein J. Org. Chem. 2021, 17, 551–557, doi:10.3762/bjoc.17.49

Graphical Abstract
  • approaches for the trifluoromethylthio (SCF3) difunctionalization of alkenes, such as cyanation [23], etherification [24][25][26][27], amination [28][29][30], chlorination [31][32], hydrogenation [33], trifluoromethylation [34], phosphonization [35], arylation [36][37][38], trifluoromethylthiolation [39
  • under irradiation of visible light [38]. In 2017, the photoredox-catalyzed intermolecular trifluoromethylthio–trifluoromethylation and thiosulfonylation reaction of unactivated alkenes have been respectively developed by Liu [34] and Xu [42]. Recently, Qing [43] and co-workers reported an efficient anti
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Published 24 Feb 2021

Synthesis of trifluoromethyl ketones by nucleophilic trifluoromethylation of esters under a fluoroform/KHMDS/triglyme system

  • Yamato Fujihira,
  • Yumeng Liang,
  • Makoto Ono,
  • Kazuki Hirano,
  • Takumi Kagawa and
  • Norio Shibata

Beilstein J. Org. Chem. 2021, 17, 431–438, doi:10.3762/bjoc.17.39

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  • the trifluoromethylation procedure was explored for aromatic, aliphatic, and conjugated methyl esters. This study presents a straightforward trifluoromethylation process of various methyl esters that convert well to the corresponding trifluoromethyl ketones. The tolerance of various pharmacophores
  • under the reaction conditions was also explored. Keywords: fluoroform; greenhouse gas; HFC-23; trifluoromethyl ketones; trifluoromethylation; Introduction In recent decades, organofluorine molecules have received widespread attention in the field of medicinal chemistry [1][2][3][4]. The introduction
  • cost of target compounds [11][12][13][14][15]. Thus, the development of low-cost and straightforward chemical synthetic technologies, including fluorination and trifluoromethylation, are matters of considerable importance to pharmaceutical and agrochemical industries. Fluoroform (HCF3, HFC-23) is an
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Published 12 Feb 2021

Deoxyfluorination of acyl fluorides to trifluoromethyl compounds by FLUOLEAD®/Olah’s reagent under solvent-free conditions

  • Yumeng Liang,
  • Akihito Taya,
  • Zhengyu Zhao,
  • Norimichi Saito and
  • Norio Shibata

Beilstein J. Org. Chem. 2020, 16, 3052–3058, doi:10.3762/bjoc.16.254

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  • ]. Methodologies for the synthesis of trifluoromethyl compounds can be modestly divided into two general categories: the direct introduction of a CF3 group into the target position by trifluoromethylation [10][11], and the construction of a CF3 unit by transforming other functional groups [12][13]. Our group has
  • developed various efficient methodologies for the electrophilic [14][15], nucleophilic [16], and radical [17] trifluoromethylation reactions for more than a decade. In recent years, we also reported the direct introduction of an acyl fluoride unit into aromatic compounds by the Pd-catalyzed cross-coupling
  • they only provided two examples. In 2018, Schoenebeck and co-workers reported the decarbonylative trifluoromethylation of acyl fluorides by trifluoromethyl triethylsilane (Et3SiCF3) under Pd catalysis at high temperature (Scheme 1b) [26], although the reaction was categorized as trifluoromethylation
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Published 14 Dec 2020

Catalytic trifluoromethylation of iodoarenes by use of 2-trifluoromethylated benzimidazoline as trifluoromethylating reagent

  • Tatsuhiro Uchikura,
  • Nanami Kamiyama,
  • Taisuke Ishikawa and
  • Takahiko Akiyama

Beilstein J. Org. Chem. 2020, 16, 2442–2447, doi:10.3762/bjoc.16.198

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  • Tatsuhiro Uchikura Nanami Kamiyama Taisuke Ishikawa Takahiko Akiyama Department of Chemistry, Faculty of Science, Gakushuin University, Mejiro, Toshima-ku, Tokyo, 171-8588, Japan 10.3762/bjoc.16.198 Abstract The trifluoromethylation of iodoarenes was accomplished by use of a 2
  • ; catalysis; copper; fluorine chemistry; trifluoromethylation; Introduction The introduction of a trifluoromethyl group is one of the most attractive reactions in drug discovery [1][2]. In the past decade, trifluoromethylation reactions of aryl halides in the presence of transition-metal complexes were
  • reported [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21]. CuCF3 is a useful species for the trifluoromethylation of aryl halides and there are a number of precursors of CuCF3 for trifluoromethylation reactions. In contrast, the catalytic generation of CuCF3 was less investigated [15
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Published 30 Sep 2020

Recent developments in enantioselective photocatalysis

  • Callum Prentice,
  • James Morrisson,
  • Andrew D. Smith and
  • Eli Zysman-Colman

Beilstein J. Org. Chem. 2020, 16, 2363–2441, doi:10.3762/bjoc.16.197

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Published 29 Sep 2020

Photosensitized direct C–H fluorination and trifluoromethylation in organic synthesis

  • Shahboz Yakubov and
  • Joshua P. Barham

Beilstein J. Org. Chem. 2020, 16, 2151–2192, doi:10.3762/bjoc.16.183

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  • reactions. Keywords: C–H activation; energy transfer; fluorination; photocatalysis; photosensitization; visible light; Review 1 Introduction 1.1 Importance of direct C–H fluorination/trifluoromethylation and photosensitization in organic synthesis 1.1.1 Importance of fluorine atoms in organic molecules
  • advantages of photosensitization, it is clear that this field has attracted less attention than PRC methods. Moreover, PS TTET is a powerful method for the fluorination and trifluoromethylation of C–H bonds. We believe this may stem from the lack of dedicated reviews grouping together the theory [103][104
  • trifluoromethylation. Section 2 equips readers with the basic theory of PS TTET and provides detailed property information tables on commonly utilized PSCats in organic synthesis and especially in C–H fluorinations, grouped by their properties relevant to PS TTET. Due to the importance of moving away from transition
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Published 03 Sep 2020

Reactions of 3-aryl-1-(trifluoromethyl)prop-2-yn-1-iminium salts with 1,3-dienes and styrenes

  • Thomas Schneider,
  • Michael Keim,
  • Bianca Seitz and
  • Gerhard Maas

Beilstein J. Org. Chem. 2020, 16, 2064–2072, doi:10.3762/bjoc.16.173

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  • ], trifluoroacetaldehyde hemiaminals [16][17][18], N,O-acetals [19] and N,N-acetals [20], 2-(trifluoromethyl)-1,3-oxazolidines [21], and N-(tert-butylsulfinyl)trifluoroacetaldimine [11][22]. Other synthetic approaches to α-CF3-substituted amines include nucleophilic trifluoromethylation strategies [17], such as the
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Published 24 Aug 2020

When metal-catalyzed C–H functionalization meets visible-light photocatalysis

  • Lucas Guillemard and
  • Joanna Wencel-Delord

Beilstein J. Org. Chem. 2020, 16, 1754–1804, doi:10.3762/bjoc.16.147

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Published 21 Jul 2020

Pauson–Khand reaction of fluorinated compounds

  • Jorge Escorihuela,
  • Daniel M. Sedgwick,
  • Alberto Llobat,
  • Mercedes Medio-Simón,
  • Pablo Barrio and
  • Santos Fustero

Beilstein J. Org. Chem. 2020, 16, 1662–1682, doi:10.3762/bjoc.16.138

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  • obtained using the less reactive triphenylphosphine dicobaltpentacarbonyl complex 63 as the catalyst (Scheme 35). In a later study [72], Riera and Fustero generalized the use of trifluoromethylalkynes as substrates for the PKR. The copper-catalyzed trifluoromethylation of terminal alkynes described by Qing
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Published 14 Jul 2020

Heterogeneous photocatalysis in flow chemical reactors

  • Christopher G. Thomson,
  • Ai-Lan Lee and
  • Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125

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  • demonstrated the safe use of gaseous CF3I as a reagent for the continuous flow PRC trifluoromethylation of 5-membered heterocycles, such as N-methylpyrrole (1, Scheme 1), with a high conversion and selectivity for the monofunctionalised product 2 [62]. The system achieved full conversion for a variety of
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Published 26 Jun 2020

Photocatalyzed syntheses of phenanthrenes and their aza-analogues. A review

  • Alessandra Del Tito,
  • Havall Othman Abdulla,
  • Davide Ravelli,
  • Stefano Protti and
  • Maurizio Fagnoni

Beilstein J. Org. Chem. 2020, 16, 1476–1488, doi:10.3762/bjoc.16.123

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  • ]phenanthridine 8.6 by the trifluoromethylation of methylenecyclopropane 8.2. The reaction started with the generation of the trifluoromethyl radical via the IrIII photocatalyzed reduction of Togni’s reagent 8.1. The fluorinated radical added onto the isonitrile group present in 8.2 to give radical 8.3·, which in
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Published 25 Jun 2020

Photocatalytic trifluoromethoxylation of arenes and heteroarenes in continuous-flow

  • Alexander V. Nyuchev,
  • Ting Wan,
  • Borja Cendón,
  • Carlo Sambiagio,
  • Job J. C. Struijs,
  • Michelle Ho,
  • Moisés Gulías,
  • Ying Wang and
  • Timothy Noël

Beilstein J. Org. Chem. 2020, 16, 1305–1312, doi:10.3762/bjoc.16.111

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  • recently reported [8][9][11], for example the trifluoromethylation of hydroxyaryls [12][13][14], and the direct introduction of the -OCF3 moiety into an organometallic species [15], a diazo compound [16][17], or an unfunctionalized C–H bond (Scheme 1B). The latter method is particularly interesting
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Published 15 Jun 2020

Copper-based fluorinated reagents for the synthesis of CF2R-containing molecules (R ≠ F)

  • Louise Ruyet and
  • Tatiana Besset

Beilstein J. Org. Chem. 2020, 16, 1051–1065, doi:10.3762/bjoc.16.92

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  • -based fluorinated reagents appeared over the years as a powerful tool in various transformations for the introduction of fluorinated moieties. Such strategy has already demonstrated a significant synthetic value for the trifluoromethylation of various compounds [16][17][18][19][20][21][22][23][24][25
  • the functionalization of different classes of compounds (benzyl and vinyl bromides, 4-biphenylboronic acid, phenylacetylene for instance). From these pioneering reports of perfluoroalkylation (trifluoromethylation, pentafluoroethylation and heptafluoropropylation), several groups studied the synthesis
  • dealt with the copper-mediated perfluororalkyaltion of (hetero)aryl bromides using the previously developed PhenCuRF [69]. Although the trifluoromethylation reaction was mainly studied, the methodology was efficiently extended to the pentafluoroethylation of various heteroarenes such as pyridine
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Published 18 May 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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  • Chaudhuri [11][12][13] using well-defined copper complex 7, originally reported as a GAO mimic [20][21][22], we showed that this ability could be extended to the catalytic generation of trifluoromethyl radicals (Scheme 7) [29]. The synthetic efficiency of complex 7 in trifluoromethylation was reported on a
  • trifluoromethylation of heteroaromatics with redox-active iminosemiquinone ligands. Reversal of helical chirality upon redox stimuli and enantioselective Michael addition with a redox-reconfigurable copper catalyst. Interaction of guanidine-copper catalyst with oxygen and representative coupling products. a4 mol
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Published 24 Apr 2020

Cascade trifluoromethylthiolation and cyclization of N-[(3-aryl)propioloyl]indoles

  • Ming-Xi Bi,
  • Shuai Liu,
  • Yangen Huang,
  • Xiu-Hua Xu and
  • Feng-Ling Qing

Beilstein J. Org. Chem. 2020, 16, 657–662, doi:10.3762/bjoc.16.62

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  • and agrochemical industries [3][4][5]. Traditional methods to access these compounds mainly include halogen–fluorine exchange of halomethyl sulfides and trifluoromethylation of sulfur-containing compounds [6][7][8]. Over the last decade, tremendous efforts have been triggered to develop methods for
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Published 08 Apr 2020

Recent advances in photocatalyzed reactions using well-defined copper(I) complexes

  • Mingbing Zhong,
  • Xavier Pannecoucke,
  • Philippe Jubault and
  • Thomas Poisson

Beilstein J. Org. Chem. 2020, 16, 451–481, doi:10.3762/bjoc.16.42

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  • )(dap)2]Cl. Trifluoromethyl methoxylation of styryl derivatives using [Cu(I)(dap)2]PF6. All redox potentials are reported vs SCE. Trifluoromethylation of silyl enol ethers. Synthesis of annulated heterocycles upon oxidation with the Sauvage catalyst. Oxoazidation of styrene derivatives using [Cu(dap)2
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Published 23 Mar 2020
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