Mono or double Pd-catalyzed C–H bond functionalization for the annulative π-extension of 1,8-dibromonaphthalene: a one pot access to fluoranthene derivatives

• Nahed Ketata,
• Linhao Liu,
• Ridha Ben Salem and
• Henri Doucet

Beilstein J. Org. Chem. 2024, 20, 427–435, doi:10.3762/bjoc.20.37

• palladium-catalyzed direct intermolecular arylation, followed by a direct intramolecular arylation step. As the C–H bond activation of several benzene derivatives remains very challenging, the preparation of fluoranthenes from 1,8-dibromonaphthalene via Suzuki coupling followed by intramolecular C–H

• simplest involves 1,8-dibromonaphthalene with a double C–H bond functionalization of benzene derivatives. This method, which employs Pd-catalyzed intermolecular and then intramolecular activation of arene C–H bonds, tolerates several useful substituents on the arene, such as fluoro, chloro, methoxy

Photoredox catalysis harvesting multiple photon or electrochemical energies

• Mattia Lepori,
• Simon Schmid and
• Joshua P. Barham

Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81

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

• 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 Friedel–Crafts acylation of benzene derivatives in tunable aryl alkyl ionic

• protocols using different metal salts [25][26][27][28][29][30] and ionic liquids [31][32][33][34][35] to acylate [36][37][38][39][40][41], alkylate [42][43][44], benzylate [45][46][47] and alkenylate [48][49] different benzene derivatives. But surprisingly, a robust protocol using commercially available and

• anhydride can be varied (Scheme 3). Different benzene derivatives were successfully used in the acylation with acetic anhydride with yields between 65% and 94% (8–13). The reaction time varied between four and 72 hours and the reaction was stopped after full conversion of the benzene derivative (detected

Recent advances in the syntheses of anthracene derivatives

• Giovanni S. Baviera and
• Paulo M. Donate

Beilstein J. Org. Chem. 2021, 17, 2028–2050, doi:10.3762/bjoc.17.131

• sequential modifications [30], photocyclization of divinylterphenyl derivatives [31], tandem radical cyclization of (Z,Z)-1,4-bis(2-iodostyryl)benzene derivatives [32], and ring-closing olefin metathesis of tetravinylterphenyls [33] as the best-known synthetic routes. Herein, we have classified the synthetic

Co-crystallization of an organic solid and a tetraaryladamantane at room temperature

• Fabian Rami,
• Jan Nowak,
• Felix Krupp,
• Wolfgang Frey and
• Clemens Richert

Beilstein J. Org. Chem. 2021, 17, 1476–1480, doi:10.3762/bjoc.17.103

• by crystallization at room temperature, using dichloromethane as solvent. Results We opted for a benzene derivative for our first foray into organic solids to be encapsulated in TAA crystals, because a number of benzene derivatives have been found in EnOCs in the past [13][14][15]. Phenol was

Synthetic approaches to bowl-shaped π-conjugated sumanene and its congeners

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 2212–2259, doi:10.3762/bjoc.16.186

• precursors for the installation of fluorine atoms using appropriate fluorinating agents such as (difluoroiodo)benzene derivatives or elemental fluorine. In the second step, when they used para-iodotoluene difluoride the reaction conversion was very low, therefore, when using Olah’s reagent (pyridine

Regioselective cobalt(II)-catalyzed [2 + 3] cycloaddition reaction of fluoroalkylated alkynes with 2-formylphenylboronic acids: easy access to 2-fluoroalkylated indenols

• Tatsuya Kumon,
• Miroku Shimada,
• Jianyan Wu,
• Shigeyuki Yamada and
• Tsutomu Konno

Beilstein J. Org. Chem. 2020, 16, 2193–2200, doi:10.3762/bjoc.16.184

• best of our knowledge, there are no reports on the practical synthesis of disubstituted 2-fluoroalkylated indenols so far. Transition-metal-catalyzed carbocyclization reactions of alkynes with benzene derivatives having a leaving group X (X = Br, I, OTs, B(OH)2) have been widely considered as one of

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

• recommend exploring the article for further details [95]. Molecules with functional groups such as carboxylic acid present complex surface topologies from bridging and bidentate binding modes [91]. Yoshida and co-workers studied the adsorption of benzene derivatives on TiO2 surfaces by solid-state NMR and

Recent developments in photoredox-catalyzed remote ortho and para C–H bond functionalizations

• Rafia Siddiqui and
• Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 248–280, doi:10.3762/bjoc.16.26

• reduction potential of 1QuCN+* was higher than that of benzene (Eox vs SCE = 2.32 V), making the electron transfer from phenol to 1QuCN+* viable. The mechanistic pathway for the C–H hydroxylation of benzene derivatives is shown in Figure 19. On the other hand, Ohkubo et al. reported that substrates like

• of substituted phenols using QuCN. Synthesis of substituted phenols with DDQ (5). Aerobic bromination of arenes using an acridinium-based photocatalyst. Aerobic bromination of arenes with anthraquinone. Chlorination of benzene derivatives with Mes-Acr-MeClO4 (2). Chlorination of arenes with 4CzIPN

Synthesis, liquid crystalline behaviour and structure–property relationships of 1,3-bis(5-substituted-1,3,4-oxadiazol-2-yl)benzenes

• Afef Mabrouki,
• Malek Fouzai,
• Armand Soldera,
• Abdelkader Kriaa and
• Ahmed Hedhli

Beilstein J. Org. Chem. 2020, 16, 149–158, doi:10.3762/bjoc.16.17

• et al. investigated on the liquid crystalline behaviour of some bis(phenyl-1,3,4-oxadiazolyl)benzene derivatives with varied number and length of terminal alkoxy chains [32]. The authors established that the mesogenicity is strongly enhanced in materials with four long terminal alkoxy substituents

Different reactivity of phosphorylallenes under the action of Brønsted or Lewis acids: a crucial role of involvement of the P=O group in intra- or intermolecular interactions at the formation of cationic intermediates

• Stanislav V. Lozovskiy,
• Alexander Yu. Ivanov and
• Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2019, 15, 1491–1504, doi:10.3762/bjoc.15.151

• best of our knowledge, up to the moment, there are no examples for an intermolecular hydroarylation of electron-deficient allenes by benzene derivatives under the action of strong Brønsted or Lewis acids. The main goals of this work were to study transformations of various phosphorylallenes under

Multicomponent reactions (MCRs): a useful access to the synthesis of benzo-fused γ-lactams

• Edorta Martínez de Marigorta,
• Jesús M. de Los Santos,
• Ana M. Ochoa de Retana,
• Javier Vicario and
• Francisco Palacios

Beilstein J. Org. Chem. 2019, 15, 1065–1085, doi:10.3762/bjoc.15.104

• no reaction in some cases. In addition to above mentioned benzene derivatives, heteroaromatic boronic acids also worked well under the reaction conditions and provided high yields of the corresponding oxindoles 131. Finally, switching the N-substituent in the starting propiolamide 128 by a H or a Bn

Ring-closing-metathesis-based synthesis of annellated coumarins from 8-allylcoumarins

• Christiane Schultze and
• Bernd Schmidt

Beilstein J. Org. Chem. 2018, 14, 2991–2998, doi:10.3762/bjoc.14.278

• furnished the azepinocoumarin 21 in quantitative yield (Scheme 3). Conclusion In summary, we demonstrated that annellated coumarins become accessible from appropriately substituted benzene derivatives in few steps, using a microwave-promoted tandem Wittig olefination/Claisen rearrangement/cyclization

Volatiles from the hypoxylaceous fungi Hypoxylon griseobrunneum and Hypoxylon macrocarpum

• Jan Rinkel,
• Alexander Babczyk,
• Tao Wang,
• Marc Stadler and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2018, 14, 2974–2990, doi:10.3762/bjoc.14.277

• 10.3762/bjoc.14.277 Abstract The volatiles emitted by the ascomycetes Hypoxylon griseobrunneum and Hypoxylon macrocarpum (Hypoxylaceae, Xylariales) were collected by use of a closed-loop stripping apparatus (CLSA) and analysed by GC–MS. The main compound class of both species were polysubstituted benzene

• derivatives. Their structures could only be unambiguously determined by comparison to all isomers with different substitution patterns. The substitution pattern of the main compound from H. griseobrunneum, the new natural product 2,4,5-trimethylanisole, was explainable by a polyketide biosynthesis mechanism

Photocatalytic formation of carbon–sulfur bonds

• Alexander Wimmer and
• Burkhard König

Beilstein J. Org. Chem. 2018, 14, 54–83, doi:10.3762/bjoc.14.4

• arenes react well and substituted pyrroles and indoles give the corresponding sulfoxides in high yields. Less electron-rich thiophene or benzene derivatives gave low yields. Nevertheless, carbocyclic azulene afforded the respective sulfoxide in 88% yield. We propose an electrophilic aromatic substitution

CF₃SO₂X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation and chlorination. Part 2: Use of CF₃SO₂Cl

• Hélène Chachignon,
• Hélène Guyon and
• Dominique Cahard

Beilstein J. Org. Chem. 2017, 13, 2800–2818, doi:10.3762/bjoc.13.273

• derivatives. Morevover, the scope could be extended to other substrates of interest, such as activated benzene derivatives and thiols. Similarly, Lu, Zhao and co-workers found out that excellent yields could also be achieved for indole derivatives when replacing PMe3 or (EtO)2P(O)H by cheap and stable

Synthesis of 1-indanones with a broad range of biological activity

• Marika Turek,
• Dorota Szczęsna,
• Marek Koprowski and
• Piotr Bałczewski

Beilstein J. Org. Chem. 2017, 13, 451–494, doi:10.3762/bjoc.13.48

• 174 followed by a Friedel–Crafts cyclization in the presence of concentrated H2SO4. The [14C]1-indanone 175 was then converted in three steps to [14C]indene 176 (Scheme 50). The same reaction sequence involving the Friedel–Crafts acylation of disubstituted benzene derivatives 177 with 3

Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates

• Mohammad Haji

Beilstein J. Org. Chem. 2016, 12, 1269–1301, doi:10.3762/bjoc.12.121

• 115. However, electron-rich heterocyclic Kabachnik–Fields adducts were found to be unreactive towards Lewis acid catalyzed cyclization processes. On the other hand, benzene derivatives 109 can participate in both cyclization modes depending on the catalyst’s nature. They either can cyclize to give the

Iridium/N-heterocyclic carbene-catalyzed C–H borylation of arenes by diisopropylaminoborane

• Mamoru Tobisu,
• Takuya Igarashi and
• Naoto Chatani

Beilstein J. Org. Chem. 2016, 12, 654–661, doi:10.3762/bjoc.12.65

• failed to form the borylated product under the current conditions. We next turned our attention to the borylation of benzene derivatives. Unfortunately, benzene derivatives proved to be much less reactive than heteroarenes when borylated with 1g. For example, Ir/ICy-catalyzed borylation of benzene with

Study on the synthesis of the cyclopenta[f]indole core of raputindole A

• Nils Marsch,
• Mario Kock and
• Thomas Lindel

Beilstein J. Org. Chem. 2016, 12, 334–342, doi:10.3762/bjoc.12.36

• , which points at a shielding effect of the TIPS group towards the indole 7-position. Since the SnCl4-mediated cyclization yields with indoles were much lower than those obtained with benzene derivatives, we investigated the behavior of indolines which lack the reactive enamine moiety. We also abandoned

Novel biphenyl-substituted 1,2,4-oxadiazole ferroelectric liquid crystals: synthesis and characterization

• Mahabaleshwara Subrao,
• Dakshina Murthy Potukuchi,
• Girish Sharada Ramachandra,
• Poornima Bhagavath,
• Sangeetha G. Bhat and
• Srinivasulu Maddasani

Beilstein J. Org. Chem. 2015, 11, 233–241, doi:10.3762/bjoc.11.26

• melting point (at ambient temperatures) and exhibit the LC phases over a wide range of temperatures. It is found in the literature [29] that the unsymmetrically substituted benzene derivatives with a biphenyl moiety possess low melting points. Hence, presently we made a methodical attempt to synthesize

Synthesis of uniform cyclodextrin thioethers to transport hydrophobic drugs

• Lisa F. Becker,
• Dennis H. Schwarz and
• Gerhard Wenz

Beilstein J. Org. Chem. 2014, 10, 2920–2927, doi:10.3762/bjoc.10.310

• affinity towards rocuronium [24][25]. Furthermore, hydrophilic γ-CD thioethers show high affinities to other guests such as polycyclic aromatic hydrocarbons [26], botulin [27][28], and fullerene C60 [29]. Hydrophilic β-CD thioethers also tightly complex volatile benzene derivatives leading to a significant

Removal of volatile organic compounds using amphiphilic cyclodextrin-coated polypropylene

• Ludmilla Lumholdt,
• Sophie Fourmentin,
• Thorbjørn T. Nielsen and
• Kim L. Larsen

Beilstein J. Org. Chem. 2014, 10, 2743–2750, doi:10.3762/bjoc.10.290

• in order to improve the aquatic ecosystem [1]. Later in 2008, the EU elaborated on the Water Framework Directive defining several problematic compounds, including various pesticides, endocrine disruptors, and hydrocarbons such as benzene and benzene derivatives, as compounds requiring immediate and

• VOCs would result in even higher stoichiometries. However, a stoichiometry of even 6:1 for β-CD:benzene/benzene derivatives is, of course, not caused by inclusion complex formation alone, as that would be physically impossible. The large uptake capacity of the coated PP must, therefore, be caused by

• water purification. Experimental Materials Untreated, isotactic polypropylene was kindly provided by Fibertex A/S (Aalborg, Denmark). Benzene and benzene derivatives (Table 2) were purchased from Sigma-Aldrich (St. Louis, Mo, USA). ACD derivatives were synthesised as described previously [8]. Purified

Triphenylene discotic liquid crystal trimers synthesized by Co₂(CO)₈-catalyzed terminal alkyne [2 + 2 + 2] cycloaddition

• Bin Han,
• Ping Hu,
• Bi-Qin Wang,
• Carl Redshaw and
• Ke-Qing Zhao

Beilstein J. Org. Chem. 2013, 9, 2852–2861, doi:10.3762/bjoc.9.321

• synthesis of discotic oligomers [46][47][48][49][50]. The transition metal-catalyzed [2 + 2 + 2] cycloaddition of three alkynes for the synthesis of polysubstituted benzene derivatives was studied due to its high efficiency and atomic efficiency [51]. The use of Co2(CO)8 as a catalyst has been extensively

New developments in gold-catalyzed manipulation of inactivated alkenes

• Michel Chiarucci and
• Marco Bandini

Beilstein J. Org. Chem. 2013, 9, 2586–2614, doi:10.3762/bjoc.9.294

• obtained from moderate to good yields under microwave irradiation (DCE, Scheme 17c) [54]. Additionally, the stronger Lewis acid AuCl3/AgSbF6 was documented to catalyze the Markovnikov selective hydroarylation of aryl- and alkyl olefins with less-nucleophilic benzene derivatives and thiophene in good yields

• indoles to alkenes. Intermolecular [Au(III)]-catalyzed hydroarylation of alkenes with benzene derivatives and thiophene. a) Intramolecular [Au(III)]-catalyzed hydroarylation of alkenes. b) A SEAr-type mechanism was hypothesized by the authors. Intramolecular [Au(I)]-catalyzed hydroalkylation of alkenes