Synthesis of N-acetyl diazocine derivatives via cross-coupling reaction

• Thomas Brandt,
• Pascal Lentes,
• Jeremy Rudtke,
• Michael Hösgen,
• Christian Näther and
• Rainer Herges

Beilstein J. Org. Chem. 2025, 21, 490–499, doi:10.3762/bjoc.21.36

• the switching behavior while weak +M substituents like bromine and fluorine as well as electron-poor heteroaromatic systems lead to increased thermal half-lives. An amino-substituted derivative 21 was obtained via Buchwald–Hartwig coupling with Boc-carbamate and subsequent deprotection. Amino

Synthesis and cytotoxicity studies of novel N-arylbenzo[h]quinazolin-2-amines

• Battini Veeraiah,
• Kishore Ramineni,
• Dabbugoddu Brahmaiah,
• Nangunoori Sampath Kumar,
• Hélène Solhi,
• Rémy Le Guevel,
• Chada Raji Reddy,
• Frédéric Justaud and
• René Grée

Beilstein J. Org. Chem. 2024, 20, 2592–2598, doi:10.3762/bjoc.20.218

• attractive results in this area. Keywords: Buchwald–Hartwig coupling; cytotoxicity; heterocycles; Pd catalysis; quinazolines; Introduction Nitrogen-containing heterocyclic molecules are ubiquitous in living systems. Among them, quinazolines, and especially the 4-aminoquinazolines (type A molecules, Figure

• afforded the known aldehyde 2 in 65% yield [13]. Then, reaction with guanidinium carbonate in DMA at high temperature [12], gave the desired intermediate 2-aminobenzo[h]quinazoline (3). In a final step, classical Buchwald–Hartwig coupling [14][15][16][17] with bromobenzene under the conditions described

Metal-catalyzed coupling/carbonylative cyclizations for accessing dibenzodiazepinones: an expedient route to clozapine and other drugs

• Amina Moutayakine and
• Anthony J. Burke

Beilstein J. Org. Chem. 2024, 20, 193–204, doi:10.3762/bjoc.20.19

• biologically active natural products such as BU-4664L. We are currently looking at this methodology to access some of these targets, including the agrochemical boscalid. Experimental Synthesis of o-(2-bromophenyl)aminoaniline (3a) Via Buchwald–Hartwig coupling: o-Phenylenediamine (1a, 0.05g, 1 equiv, 0.46 mmol

The effect of dark states on the intersystem crossing and thermally activated delayed fluorescence of naphthalimide-phenothiazine dyads

• Liyuan Cao,
• Xi Liu,
• Xue Zhang,
• Jianzhang Zhao,
• Fabiao Yu and
• Yan Wan

Beilstein J. Org. Chem. 2023, 19, 1028–1046, doi:10.3762/bjoc.19.79

• chromophores, which are coupled through a Buchwald–Hartwig coupling reaction (another NI-PTZ paper) [39]. The oxidation of the PTZ unit was readily performed by treatment with H2O2 as oxidant (Scheme 1). All compounds were obtained with satisfactory yields and the molecular structures were fully characterized

Ionic multiresonant thermally activated delayed fluorescence emitters for light emitting electrochemical cells

• Merve Karaman,
• Abhishek Kumar Gupta,
• Subeesh Madayanad Suresh,
• Tomas Matulaitis,
• Lorenzo Mardegan,
• Daniel Tordera,
• Henk J. Bolink,
• Sen Wu,
• Stuart Warriner,
• Ifor D. Samuel and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2022, 18, 1311–1321, doi:10.3762/bjoc.18.136

• synthetic strategy, which itself was synthesized from Br-DiKTa [28] following a Buchwald–Hartwig coupling. Details of the synthesis are found in Supporting Information File 1. The identity and purity of the molecules were verified using a combination of 1H and 13C NMR spectroscopy, high resolution mass

Synthesis of 10-O-aryl-substituted berberine derivatives by Chan–Evans–Lam coupling and investigation of their DNA-binding properties

• Peter Jonas Wickhorst,
• Mathilda Blachnik,
• Denisa Lagumdzija and
• Heiko Ihmels

Beilstein J. Org. Chem. 2021, 17, 991–1000, doi:10.3762/bjoc.17.81

• substitution [17][18][19][20][21] of berberrubine (1b) have been performed, whereas the direct O-arylation of berberrubine has not been accomplished, yet, most likely because the substrate is not fully compatible with the usual conditions of the corresponding Ullmann or Buchwald–Hartwig coupling reactions

Synthesis and characterization of bis(4-amino-2-bromo-6-methoxy)azobenzene derivatives

• David Martínez-López,
• Amirhossein Babalhavaeji,
• Diego Sampedro and
• G. Andrew Woolley

Beilstein J. Org. Chem. 2019, 15, 3000–3008, doi:10.3762/bjoc.15.296

• were then replaced by amino substituents using a Buchwald–Hartwig coupling [20]. Since calculations predicted that 5- and 6-membered rings would have similar effects on the positions of the absorption maxima, we opted to use 6-membered rings, specifically a morpholino substituent and a piperazino

Rational design of boron-dipyrromethene (BODIPY) reporter dyes for cucurbit[7]uril

• Mohammad A. Alnajjar,
• Jürgen Bartelmeß,
• Robert Hein,
• Pichandi Ashokkumar,
• Mohamed Nilam,
• Werner M. Nau,
• Knut Rurack and
• Andreas Hennig

Beilstein J. Org. Chem. 2018, 14, 1961–1971, doi:10.3762/bjoc.14.171

• the aminomethyladamantane derivative 5, a route via a bromophenyl-BODIPY BDP-Br followed by a Buchwald–Hartwig coupling was performed. For the latter, a previously published Pd/XPhos containing catalytic system was successfully utilized (route D) [39]. Spectroscopic characterization of dyes To ensure

Synthesis of substituted Z-styrenes by Hiyama-type coupling of oxasilacycloalkenes: application to the synthesis of a 1-benzoxocane

• James R. Vyvyan,
• Courtney A. Engles,
• Scott L. Bray,
• Erik D. Wold,
• Christopher L. Porter and
• Mikhail O. Konev

Beilstein J. Org. Chem. 2017, 13, 2122–2127, doi:10.3762/bjoc.13.209

• established in applying the Buchwald–Hartwig coupling to 15, producing the benzoxocane 24, which contains the carbon skeleton of heliannuol A. Retrosynthetic analysis of heliannuol A. Hydrosilylation of alkynols. Hydrogenation of benzoxocane 24. Pd-catalyzed couplings of oxasilacycloalkenes with aryl iodides

Facile synthesis of indolo[3,2-a]carbazoles via Pd-catalyzed twofold oxidative cyclization

• Chao Yang,
• Kai Lin,
• Lan Huang,
• Wei-dong Pan and
• Sheng Liu

Beilstein J. Org. Chem. 2016, 12, 2490–2494, doi:10.3762/bjoc.12.243

• designed sequence, it would allow us to establish a novel and simple route to indolo[3,2-a]carbazole derivatives. Our investigation started with the preparation of methyl 2,4-dianilinobenzoates (2a–e, Scheme 2). The double Buchwald–Hartwig coupling of methyl 2,4-dibromobenzoate 3 (obtained by treatment of

Catalytic Chan–Lam coupling using a ‘tube-in-tube’ reactor to deliver molecular oxygen as an oxidant

• Carl J. Mallia,
• Paul M. Burton,
• Alexander M. R. Smith,
• Gary C. Walter and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2016, 12, 1598–1607, doi:10.3762/bjoc.12.156

• improvements achieved with the Buchwald–Hartwig coupling, limitations such as sensitivity to air and moisture, functional group tolerance and the high cost of palladium, reignited the search for an improved method. In 1998, the groups of Chan [8], Evans [9] and Lam [10] independently reported upon mild methods

The synthesis of active pharmaceutical ingredients (APIs) using continuous flow chemistry

• Marcus Baumann and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2015, 11, 1194–1219, doi:10.3762/bjoc.11.134

• inhibitor Gleevec [53][54][55]. Reported by the Innovative Technology Centre (ITC) in 2010, this landmark synthesis was realised as a continuous process featuring an amide formation, a nucleophilic substitution and a Buchwald–Hartwig coupling as key synthesis steps performed in flow (Scheme 4). Further

• application of this new concept was demonstrated in the flow synthesis of the atypical neurolepticum olanzapine (121) [104]. The synthesis begins with a Buchwald–Hartwig coupling between 2-iodonitrobenzene (122) and 2-aminothiophene 123 enabled by inductive heating (Scheme 21). After in-line extraction and

Exploration of C–H and N–H-bond functionalization towards 1-(1,2-diarylindol-3-yl)tetrahydroisoquinolines

• Michael Ghobrial,
• Marko D. Mihovilovic and
• Michael Schnürch

Beilstein J. Org. Chem. 2014, 10, 2186–2199, doi:10.3762/bjoc.10.226

• wanted to use direct functionalization either via C–H activation or cross dehydrogenative coupling for C–C-bond-forming reactions avoiding the use of two prefunctionalized building blocks. Naturally, C–N-bond formation should proceed via Buchwald–Hartwig coupling. The target molecules can be considered

• –Hartwig coupling; C–C coupling; C–H functionalization; iron catalysis; regioselective arylation; Introduction 1,2,3,4-Tetrahydroisoquinolines (THIQs) are common substructures in natural products [1]. The structural motif of 1-(indol-3-yl)-THIQ is also found in compounds with biological activity, for

• -diarylindoles were successfully reacted with N-Boc-THIQ to furnish 1,2,3-trisubstituted indoles as target compounds. Furthermore, regioselective N-arylation of protected and unprotected 1-(indol-3-yl)-THIQs was successfully conducted using either simple iron or copper salts as catalysts. Keywords: Buchwald

Camera-enabled techniques for organic synthesis

• Steven V. Ley,
• Richard J. Ingham,
• Matthew O’Brien and
• Duncan L. Browne

Beilstein J. Org. Chem. 2013, 9, 1051–1072, doi:10.3762/bjoc.9.118

• is visible with the aid of the video camera; (d) a still from the footage showing arcing observed as a bright flash of light. Video stills reprinted from [47], Copyright 2008, with permission from Elsevier. (a) Buchwald–Hartwig coupling within a microchannel reactor. (b) Camera view of aggregate