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Search for "Friedel–Crafts" in Full Text gives 190 result(s) in Beilstein Journal of Organic Chemistry.

Cu(OTf)2-catalyzed multicomponent reactions

  • Sara Colombo,
  • Camilla Loro,
  • Egle M. Beccalli,
  • Gianluigi Broggini and
  • Marta Papis

Beilstein J. Org. Chem. 2025, 21, 122–145, doi:10.3762/bjoc.21.7

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  • involves a FriedelCrafts alkylation of the arene followed by hydroamination (Scheme 6) [5]. The mechanism plausibly starts with the in situ formation of triflic acid from Cu(OTf)2 which leads to protonation of the oxygen atom of the alcohol with generation of the activated allyl alcohol. This latter gives
  • the allyl carbenium ion VI through the loss of a molecule of water, then undergoes a FriedelCrafts alkylation by attack of the aromatic partner. The outcome of the reaction proceeds through a Markovnikov protonation of the allylated arene VII by triflic acid, which generates the carbocation
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Published 14 Jan 2025

Synthesis of acenaphthylene-fused heteroarenes and polyoxygenated benzo[j]fluoranthenes via a Pd-catalyzed Suzuki–Miyaura/C–H arylation cascade

  • Merve Yence,
  • Dilgam Ahmadli,
  • Damla Surmeli,
  • Umut Mert Karacaoğlu,
  • Sujit Pal and
  • Yunus Emre Türkmen

Beilstein J. Org. Chem. 2024, 20, 3290–3298, doi:10.3762/bjoc.20.273

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  • ][27], as well as FriedelCrafts [28] and Prins-type [29] reactions have been developed to date [2]. However, methods that enable access to the analogous acenaphthylene-fused heteroarenes are less common [30][31][32][33][34][35][36][37][38][39]. In one such study, Würthner and co-workers reported a Pd
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Published 23 Dec 2024

Non-covalent organocatalyzed enantioselective cyclization reactions of α,β-unsaturated imines

  • Sergio Torres-Oya and
  • Mercedes Zurro

Beilstein J. Org. Chem. 2024, 20, 3221–3255, doi:10.3762/bjoc.20.268

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  • authors proposed a possible mechanism for the reaction which is depicted in Scheme 20. The chiral phosphoric acid activates both the azoalkene acting as a Brønsted acid and the indole acting as a Lewis base promoting a FriedelCrafts-type 1,4-addition of the indole to the azoalkene. In this manner, a
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Published 10 Dec 2024

N-Glycosides of indigo, indirubin, and isoindigo: blue, red, and yellow sugars and their cancerostatic activity

  • Peter Langer

Beilstein J. Org. Chem. 2024, 20, 2840–2869, doi:10.3762/bjoc.20.240

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  • described above, glycosides 81 were inactive against cancer and melanoma cell lines. 3,3-Diaryloxindole-N-glycosides The FriedelCrafts acylation of isatin-N-rhamnoside β-16a with benzene (82a) afforded 3,3-diphenyloxindole-N-rhamnoside β-83a in 94% yield (Scheme 44) [63]. Deprotection of the latter
  • afforded β-84a in 88% yield. FriedelCrafts acylation of isatin-N-glycosides β-16c–e with benzene, toluene, anisole, and N,N-dimethylaniline and subsequent deprotection afforded 3,3-diaryloxindole-N-glycosides β-84b–l (Scheme 45) [63]. Some of the products showed antiproliferative activity against
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Published 08 Nov 2024

Transition-metal-free decarbonylation–oxidation of 3-arylbenzofuran-2(3H)-ones: access to 2-hydroxybenzophenones

  • Bhaskar B. Dhotare,
  • Seema V. Kanojia,
  • Chahna K. Sakhiya,
  • Amey Wadawale and
  • Dibakar Goswami

Beilstein J. Org. Chem. 2024, 20, 2655–2667, doi:10.3762/bjoc.20.223

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  • reported over the years (Figure 2) [2]. Conventionally, benzophenones are synthesized by FriedelCrafts acylation of benzoyl halides and aromatic compounds. However, the regioselectivity of FriedelCrafts benzoylation at the desired position is difficult to control [9]. On the other hand, 2
  • synthetic route. Results and Discussion Initially, 3-arylbenzofuran-2(3H)-ones 3aa–ma were prepared following a SbCl3-catalyzed FriedelCrafts alkylation of phenols 1a–m with benzylic alcohols 2a–d, earlier reported by us (Scheme 1) [21][22][23]. All the synthesized 3-arylbenzofuran-2(3H)-ones were
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Published 21 Oct 2024

Catalysing (organo-)catalysis: Trends in the application of machine learning to enantioselective organocatalysis

  • Stefan P. Schmid,
  • Leon Schlosser,
  • Frank Glorius and
  • Kjell Jorner

Beilstein J. Org. Chem. 2024, 20, 2280–2304, doi:10.3762/bjoc.20.196

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  • descriptors, Asahara and Miyao [108] considered different CPA-catalysed nucleophilic additions to imines, comprising aza-Mannich reactions and FriedelCrafts reactions among others. Different reactions were also combined by Liles et al. [124]. For a transfer hydrogenation reaction, the authors used a workflow
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Published 10 Sep 2024

Selective hydrolysis of α-oxo ketene N,S-acetals in water: switchable aqueous synthesis of β-keto thioesters and β-keto amides

  • Haifeng Yu,
  • Wanting Zhang,
  • Xuejing Cui,
  • Zida Liu,
  • Xifu Zhang and
  • Xiaobo Zhao

Beilstein J. Org. Chem. 2024, 20, 2225–2233, doi:10.3762/bjoc.20.190

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  • ][62][63][64], we conducted research on their organic reactions in water and reported some good results, such as thioacetalization using ketene dithioacetals as odorless thiol equivalent [65], FriedelCrafts alkylation of cyclic ketene dithioacetals with alcohols [66], the hydrolysis of chain α-oxo
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Published 03 Sep 2024

Novel truxene-based dipyrromethanes (DPMs): synthesis, spectroscopic characterization and photophysical properties

  • Shakeel Alvi and
  • Rashid Ali

Beilstein J. Org. Chem. 2024, 20, 2163–2170, doi:10.3762/bjoc.20.186

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  • for diverse applications in future studies. Keywords: condensation; co-timerization; dipyrromethane; FriedelCrafts acylation; heterocycles; pyrrole; truxene; Introduction The scaffold of truxene (10,15‐dihydro‐5H‐diindeno[1,2‐a;1′,2′‐c]fluorene) and its congeners comprises three fluorene subunits
  • derivatives (12, 15, and 17) in controlled manner (with appropriate equivalents of acetyl chloride and aluminium chloride) using one-to-threefold FriedelCrafts acylation reaction(s) at 0 °C to rt in dichloromethane (DCM) solvent (Scheme 1 and Scheme 2). Subsequent condensation of thus prepared acetylated
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Published 29 Aug 2024

The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023)

  • Cristina Martini,
  • Muhammad Idham Darussalam Mardjan and
  • Andrea Basso

Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162

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Published 01 Aug 2024

Chemo-enzymatic total synthesis: current approaches toward the integration of chemical and enzymatic transformations

  • Ryo Tanifuji and
  • Hiroki Oguri

Beilstein J. Org. Chem. 2024, 20, 1693–1712, doi:10.3762/bjoc.20.151

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  • bisorbicillinoid family. Substrate 33 for SorbC-catalyzed enzymatic transformation was synthesized in 3 steps from phenol 35 via formylation and subsequent reduction to introduce a methyl group, followed by a FriedelCrafts acylation with 36 (Scheme 4B) [39][40]. The in vitro enzymatic transformation of 33 by
  • -workers [65][66][67], facilitated an intramolecular FriedelCrafts-type homo-dimerization and led to the efficient construction of the 22-membered paracyclophane scaffold. Of several sophisticated chemo-enzymatic strategies, this review highlights the total syntheses of tylactone (4) and juvenimicins
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Published 23 Jul 2024

Synthesis of 2-benzyl N-substituted anilines via imine condensation–isoaromatization of (E)-2-arylidene-3-cyclohexenones and primary amines

  • Lu Li,
  • Na Li,
  • Xiao-Tian Mo,
  • Ming-Wei Yuan,
  • Lin Jiang and
  • Ming-Long Yuan

Beilstein J. Org. Chem. 2024, 20, 1468–1475, doi:10.3762/bjoc.20.130

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  • additives in the petrochemical industry [3]. Besides, 2-benzylanilines also serve as valuable building blocks in synthetic chemistry [4]. The classical route to this kind of aniline derivatives usually starts from parent anilines, which undergo FriedelCrafts reaction with acyl halides followed by carbonyl
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Published 02 Jul 2024

Bismuth(III) triflate: an economical and environmentally friendly catalyst for the Nazarov reaction

  • Manoel T. Rodrigues Jr.,
  • Aline S. B. de Oliveira,
  • Ralph C. Gomes,
  • Amanda Soares Hirata,
  • Lucas A. Zeoly,
  • Hugo Santos,
  • João Arantes,
  • Catarina Sofia Mateus Reis-Silva,
  • João Agostinho Machado-Neto,
  • Leticia Veras Costa-Lotufo and
  • Fernando Coelho

Beilstein J. Org. Chem. 2024, 20, 1167–1178, doi:10.3762/bjoc.20.99

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  • ][8][9][10][11][12]. The interest in the preparation of functionalized indanone derivatives has increased enormously, and many synthetic methods have been developed, including FriedelCrafts cyclization reactions [13], cyclization of acetylenic derivatives [14], ring contractions and ring expansions
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Published 21 May 2024
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  • substituents, respectively, were also attempted but without success. In these cases, the sterically congesting ortho isopropyl and tert-butyl groups stymie the FriedelCrafts acylation step leading to diketone (Scheme 1). Experimental and computational studies of 1,3-diarylisoacenofurans Purified
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Published 17 May 2024

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

  • Periklis X. Kolagkis,
  • Eirini M. Galathri and
  • Christoforos G. Kokotos

Beilstein J. Org. Chem. 2024, 20, 379–426, doi:10.3762/bjoc.20.36

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  • reaction between aldehydes with indoles, while focusing on the more environmentally friendly methods developed over the years. Keywords: aldehyde; BIMs; FriedelCrafts reaction; green chemistry; indole; Review Medicinal properties In recent years, diindolylmethane (DIM, 1) and its derivatives known as
  • associated with low catalyst loading, extremely high efficiency and broad substrate scope and the possibility of use of both organic solvents or water, with the drawback however, of the employment of conventional heating [92]. In 2019, Toy et al. proposed an alternative approach for the FriedelCrafts
  • with one another. With the new avenues offered by the advent of nanocatalysis, it did not take long for its application in the FriedelCrafts arylation of indoles with aldehydes, since the development of more resource-efficient catalytic pathways for the synthesis of BIMs had received great interest
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Published 22 Feb 2024

Tandem Hock and Friedel–Crafts reactions allowing an expedient synthesis of a cyclolignan-type scaffold

  • Viktoria A. Ikonnikova,
  • Cristina Cheibas,
  • Oscar Gayraud,
  • Alexandra E. Bosnidou,
  • Nicolas Casaretto,
  • Gilles Frison and
  • Bastien Nay

Beilstein J. Org. Chem. 2024, 20, 162–169, doi:10.3762/bjoc.20.15

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  • benzyl moiety on the substrate resulted in tandem FriedelCrafts reactions to form the 1-aryltetraline products. These compounds share a close analogy to the cyclolignan natural products. Experimental observations and a DFT study support the involvement of an aldehyde intermediate during the Friedel
  • Crafts reactions, rather than an oxocarbenium. Keywords: 1-aryltetralines; FriedelCrafts reaction; Hock rearrangement; oxidative cleavage; tandem reactions; Introduction The Hock cleavage [1] consists in the acid-catalyzed rearrangement of organic hydroperoxides, leading to the oxidative cleavage of a
  • ), successively involving a Schenck-ene photooxygenation of an alkene A, an acid-catalyzed Hock cleavage of hydroperoxide B generating an aldehyde derivative C, and an acid-catalyzed FriedelCrafts reaction in the presence of an aromatic nucleophile leading to D [17]. In principle, a second FriedelCrafts
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Published 25 Jan 2024

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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  • ], FriedelCrafts acylation [12], radical cascade reactions [2][13], and photoinduced radical cyclizations [14][15][16][17]. However, these methods often suffer from drawbacks such as harsh reaction conditions and the requirement of transition-metal catalysts. Although photocatalyzed cyclization reactions
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Published 19 Jan 2024

Non-noble metal-catalyzed cross-dehydrogenation coupling (CDC) involving ether α-C(sp3)–H to construct C–C bonds

  • Hui Yu and
  • Feng Xu

Beilstein J. Org. Chem. 2023, 19, 1259–1288, doi:10.3762/bjoc.19.94

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  • catalyst. The authors demonstrated that the introduction of the two indoles occurs in two distinct steps, a radical process and a FriedelCrafts alkylation reaction. Coumarin and flavonoid derivatives are very valuable precursors in drug synthesis. In 2015, Ge et al. developed the regioselective and atom
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Published 06 Sep 2023

Synthesis of tetrahydrofuro[3,2-c]pyridines via Pictet–Spengler reaction

  • Elena Y. Mendogralo and
  • Maxim G. Uchuskin

Beilstein J. Org. Chem. 2023, 19, 991–997, doi:10.3762/bjoc.19.74

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  • the use of 3-substituted furans. For example, the intramolecular FriedelCrafts alkylation reaction (Scheme 1a) of alcohols [9][10][11], alkenes [12] or acetylenes [13] affords the desired tetrahydrofuro[3,2-c]pyridines. A related method is based on a Au(I)-catalyzed domino sequence dearomatization
  • /ipso-cyclization/Michael-type FriedelCrafts alkylation (Scheme 1b) [14][15][16]. Unfortunately, approaches including the intramolecular alkylation of 3-substituted furans are underinvestigated as these substrates are usually hard to reach and the resulting benzyl carbocation is often prone to undergo
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Published 30 Jun 2023
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  • Anup Biswas Department of Chemistry, Hooghly Women’s College, Vivekananda Road, Pipulpati, Hooghly - 712103, WB, India 10.3762/bjoc.19.72 Abstract The aza-FriedelCrafts reaction allows an efficient coupling of electron-rich aromatic systems with imines for the facile incorporation of aminoalkyl
  • groups into the aromatic ring. This reaction has a great scope of forming aza-stereocenters which can be tuned by different asymmetric catalysts. This review assembles recent advances in asymmetric aza-FriedelCrafts reactions mediated by organocatalysts. The mechanistic interpretation with the origin of
  • stereoselectivity is also explained. Keywords: asymmetric; aza-FriedelCrafts reaction; H-bonding; organocatalysis; stereoselectivity; Introduction The ease of a chemical transformation depends on the thermodynamic instability of a chemical bond owing to its fast cleavage under mild reaction conditions. A C–H
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Published 28 Jun 2023

Pyridine C(sp2)–H bond functionalization under transition-metal and rare earth metal catalysis

  • Haritha Sindhe,
  • Malladi Mounika Reddy,
  • Karthikeyan Rajkumar,
  • Akshay Kamble,
  • Amardeep Singh,
  • Anand Kumar and
  • Satyasheel Sharma

Beilstein J. Org. Chem. 2023, 19, 820–863, doi:10.3762/bjoc.19.62

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  • . In addition, the lone pair electrons of the nitrogen atom interact with Lewis acids instead of the π-electrons of the ring system thus resulting to its reduced reactivity for electrophilic aromatic substitution reactions, such as a FriedelCrafts reaction [21][22][23]. Hence, it is challenging to
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Published 12 Jun 2023

Sulfate radical anion-induced benzylic oxidation of N-(arylsulfonyl)benzylamines to N-arylsulfonylimines

  • Joydev K. Laha,
  • Pankaj Gupta and
  • Amitava Hazra

Beilstein J. Org. Chem. 2023, 19, 771–777, doi:10.3762/bjoc.19.57

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  • their unique stability, defined reactivity, and versatility in organic synthesis [2]. Leveraging their electron-deficient nature, N-arylsulfonylimines are widely used in organic transformations including nucleophilic addition, cycloaddition, imino-aldol reaction, ene reactions, aza-FriedelCrafts
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Published 05 Jun 2023

Friedel–Crafts acylation of benzene derivatives in tunable aryl alkyl ionic liquids (TAAILs)

  • Swantje Lerch,
  • Stefan Fritsch and
  • Thomas Strassner

Beilstein J. Org. Chem. 2023, 19, 212–216, doi:10.3762/bjoc.19.20

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  • Swantje Lerch Stefan Fritsch Thomas Strassner Professur für Physikalische Organische Chemie, Technische Universität Dresden, 01062 Dresden, Germany 10.3762/bjoc.19.20 Abstract An iron(III) chloride hexahydrate-catalyzed FriedelCrafts acylation of benzene derivatives in tunable aryl alkyl ionic
  • liquids (TAAILs) has been developed. Through optimization of the metal salt, reaction conditions and ionic liquids, we were able to design a robust catalyst system that tolerates different electron-rich substrates under ambient atmosphere and allows for a multigram scale. Keywords: FriedelCrafts
  • acylation; homogeneous catalysis; ionic liquids; iron catalysis; TAAILs; Introduction The FriedelCrafts acylation is one of the oldest metal-catalyzed reactions in organic chemistry [1] and allows for the synthesis of a broad range of diverse compounds [2][3][4][5]. Starting from electron-rich aromatic
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Published 23 Feb 2023

1,4-Dithianes: attractive C2-building blocks for the synthesis of complex molecular architectures

  • Bram Ryckaert,
  • Ellen Demeyere,
  • Frederick Degroote,
  • Hilde Janssens and
  • Johan M. Winne

Beilstein J. Org. Chem. 2023, 19, 115–132, doi:10.3762/bjoc.19.12

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  • reactions, as pseudo-heteroarylzinc reagents. Another example developed by Knochel uses the zincated 1,4-dithiin 22 as a nucleophile to add across the N–O bond in anthranil [44], which spontaneously cyclizes to a heterocycle-fused quinoline via a FriedelCrafts-type pathway onto the released aldehyde moiety
  • dependence [95]. On the other hand, simple benzyl cations can undergo more controlled (3 + 2) annulations, as is illustrated by the long-known FriedelCrafts-type acid-catalyzed cascade reaction of styrene leading to the cyclic styrene dimer 86 (Scheme 13c) [96][97]. This (3 + 2) cycloaddition reactivity of
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Published 02 Feb 2023

Two-step continuous-flow synthesis of 6-membered cyclic iodonium salts via anodic oxidation

  • Julian Spils,
  • Thomas Wirth and
  • Boris J. Nachtsheim

Beilstein J. Org. Chem. 2023, 19, 27–32, doi:10.3762/bjoc.19.2

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  • FriedelCrafts alkylation followed by an anodic oxidative cyclization yielded a defined set of cyclic iodonium salts in a highly substrate-dependent yield. Keywords: electrochemistry; flow chemistry; hypervalent compounds; iodine; oxidation; Introduction Hypervalent iodine compounds (HVI) are well
  • , we improved the formation of iodoarenes through a Brønsted acid-mediated FriedelCrafts reaction followed by an oxidative cyclization to form the desired CDIS 1 (Scheme 1A). This one-pot approach is based on ortho-iodinated benzyl alcohols as starting materials. It allows access to a variety of
  • the FriedelCrafts reaction via GC analysis. Both steps in series resulted in successful product formation with an albeit slightly diminished yield of 49% (Table 3, entry 3). We increased the yield to 54% by introducing an electrolyte (Table 3, entry 2). A further current increase had no beneficial
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Published 03 Jan 2023

Combining the best of both worlds: radical-based divergent total synthesis

  • Kyriaki Gennaiou,
  • Antonios Kelesidis,
  • Maria Kourgiantaki and
  • Alexandros L. Zografos

Beilstein J. Org. Chem. 2023, 19, 1–26, doi:10.3762/bjoc.19.1

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  • to synthesize more than 4 g of the natural product (+)-yahazunol (61). (+)-Yahazunol (61) can be readily transformed to several members of meroterpenoids of the class, either by FriedelCrafts reactions or common oxidative manipulations. Total synthesis of dysideanone B (75) and dysiherbol A (79) (Lu
  • aromatic common intermediate 9 (Scheme 10). Despite the simplicity, the most obvious disconnections, such as an anionic enone conjugated addition and a direct cationic FriedelCrafts reaction failed. Highlighting the power of radical disconnection, the group thought of utilizing a β-keto carbon-centered
  • radical to circumvent the unsuccessful FriedelCrafts reaction. Prior reports implicated β-keto radical formation in the ring opening of siloxycyclopropanes with photoinduced electron transfer (PET) to 1,4-dicyanonaphthalene [65]. Inspired by reports on dual photoredox and Ni-catalytic cross-coupling
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Published 02 Jan 2023
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