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

• -acetyl diazocine system could be achieved via Suzuki coupling reactions in high yields (7, 9–14, 17) as well as the vinylation via Stille coupling (8). These compounds also exhibit excellent switching properties. Electron-withdrawing substituents at the aryl substituents have no significant influence on

Photomechanochemistry: harnessing mechanical forces to enhance photochemical reactions

• Francesco Mele,
• Ana M. Constantin,
• Andrea Porcheddu,
• Raimondo Maggi,
• Giovanni Maestri,
• Nicola Della Ca’ and
• Luca Capaldo

Beilstein J. Org. Chem. 2025, 21, 458–472, doi:10.3762/bjoc.21.33

• . Also in this case, the addition of toluene was beneficial and excellent yield of the corresponding product (10.2) was observed in 30 h of reaction. As a comparison, the latter reaction required 48 h in solution. Intriguingly, 10.3 could in turn be synthesized via a mechanochemical Suzuki coupling

Synthesis, structure and π-expansion of tris(4,5-dehydro-2,3:6,7-dibenzotropone)

• Yongming Xiong,
• Xue Lin Ma,
• Shilong Su and
• Qian Miao

Beilstein J. Org. Chem. 2025, 21, 1–7, doi:10.3762/bjoc.21.1

•  1) featuring three heptagons and two pentagons, with its structure confirmed by X-ray crystallography. This π-expansion approach of compound 1 differs from the method reported by Müllen and co-workers, which involves Ramirez olefination and Suzuki coupling, resulting in the expansion of a seven

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

• ) was synthesized via consecutive Suzuki coupling and Scholl reaction in a total yield of 77%. The synthesis, molecular structures, nomenclature, and synthetic yields of all compounds are shown in general Scheme 1. All prepared molecules were fully characterized by NMR (1H, 19F and 13C), HRMS, and CHN

Cyclodextrin-based rotaxanes for polymer materials: challenge on simultaneous realization of inexpensive production and defined structures

• Yosuke Akae

Beilstein J. Org. Chem. 2024, 20, 3026–3049, doi:10.3762/bjoc.20.252

• substitution/addition reactions became the standard for end-capping reactions, although a transition metal–catalyzed cross-coupling reaction has also been used to synthesize CD-based rotaxane. Typically, water-soluble components are prepared, after which the Suzuki coupling reaction in water is used to

• α-CD-based rotaxane comprising a stilbene axle that was synthesized by the Suzuki coupling reaction to light irradiation (Figure 6, right) [58]. In this structure, α-CD was first located on the trans-stilbene moiety, after which it moved to the benzene ring moiety via the cis-isomerization of the

Recent advances in transition-metal-free arylation reactions involving hypervalent iodine salts

• Ritu Mamgain,
• Kokila Sakthivel and
• Fateh V. Singh

Beilstein J. Org. Chem. 2024, 20, 2891–2920, doi:10.3762/bjoc.20.243

• to good yields of the corresponding products. The vinyl boronates obtained from the aforementioned reaction were subsequently subjected to a Suzuki coupling with the remaining aryl iodides obtained from 16 in the presence of a palladium catalyst. This step facilitated the formation of functionalized

C–C Coupling in sterically demanding porphyrin environments

• Liam Cribbin,
• Brendan Twamley,
• Nicolae Buga,
• John E. O’ Brien,
• Raphael Bühler,
• Roland A. Fischer and
• Mathias O. Senge

Beilstein J. Org. Chem. 2024, 20, 2784–2798, doi:10.3762/bjoc.20.234

• porphyrins [34] and tetrabromoanthracenyl porphyrins [35]. In general, the halogen atom needed for the Suzuki coupling reaction resides on the porphyrin; however, Suzuki–Miyaura reactivity has also been shown to be reversed whereby the synthesis of borolanylporphyrins leads to a different approach to

• Discussion Investigation of the Suzuki coupling reaction at the meso-phenyl position of dodecasubstituted porphyrins Synthesis of porphyrin precursors To investigate the Suzuki coupling at the ortho-, meta- and para-position of a dodecasubstituted saddle-shaped porphyrin, first the precursor porphyrins 11

• the Suzuki coupling began with investigating first the Suzuki reaction compatibility of boronic acid 14 with porphyrin 13. Porphyrin 13 and phenylboronic acid (14) were subjected to coupling at 85 °C for 48 hours using Pd2dba3/SPhos as a catalyst/ligand giving porphyrin 26 in a 32% yield, based on a

Natural resorcylic lactones derived from alternariol

• Joachim Podlech

Beilstein J. Org. Chem. 2024, 20, 2171–2207, doi:10.3762/bjoc.20.187

Multicomponent syntheses of pyrazoles via (3 + 2)-cyclocondensation and (3 + 2)-cycloaddition key steps

• Ignaz Betcke,
• Alissa C. Götzinger,
• Maryna M. Kornet and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2024, 20, 2024–2077, doi:10.3762/bjoc.20.178

• phosphane ligands is crucial for the selectivity in this reaction. Suzuki coupling can also serve for the functionalization of iodochromones 55, which, as α,β-unsaturated ketones, undergo ring opening under the reaction conditions, followed by Michael addition–cyclocondensation. Xie et al. devised a method

• Suzuki coupling of β,β-dibromenones 100, boronic acids, and 1,1-dimethylhydrazine in a three-component reaction (Scheme 36) [119]. The intermediary 5-bromopyrazoles formed by condensation/N-demethylation/cyclization sequence subsequently react by Suzuki–Miyaura cross-coupling in a one-pot fashion. The

• = Cl, Br). The resulting 4-halopyrazoles 111 can either be isolated or undergo further Suzuki coupling with arylboronic acids. Both couplings use the Pd catalyst in a sequential fashion. To increase the yields, both cyclization and Suzuki coupling are carried out with microwave support. Some of the

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

• , obtaining an enzyme-metal biohybrid catalyst [22]. The authors tested it in a one-pot GBB reaction–Suzuki coupling, employing 5-bromo-2-aminopyridine (20), benzaldehyde (2), tert-butyl isocyanide (5) and phenylboronic acid (21). Compound 22 was obtained in 87% yield by performing the GBB reaction at room

Diameter-selective extraction of single-walled carbon nanotubes by interlocking with Cu-tethered square nanobrackets

• Guoqing Cheng and
• Naoki Komatsu

Beilstein J. Org. Chem. 2024, 20, 1298–1307, doi:10.3762/bjoc.20.113

• can calculate larger system (>500 atoms) containing transition metals more precisely [16][17]. Result and Discussion Synthesis of Cu-tethered square nanobrackets 1b A pyrene-based nanobracket 4b was synthesized via a one-pot Suzuki coupling followed by the formation of dipyrrin from the dialdehyde 3

Carbonylative synthesis and functionalization of indoles

• Alex De Salvo,
• Raffaella Mancuso and
• Xiao-Feng Wu

Beilstein J. Org. Chem. 2024, 20, 973–1000, doi:10.3762/bjoc.20.87

• /carbonylation/Suzuki coupling reaction for the synthesis of 2-aroylindoles and 2-heteroaroylindoles. Pd(0)-catalyzed single isonitrile insertion: synthesis of 1-(3-amino)-1H-indol-2-yl)-1-ketones. Pd(0)-catalyzed gas-free carbonylation of 2-alkynylanilines to 1-(1H-indol-1-yl)-2-arylethan-1-ones. Pd(II

Synthesis and biological profile of 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, a novel class of acyl-ACP thioesterase inhibitors

• Jens Frackenpohl,
• David M. Barber,
• Guido Bojack,
• Birgit Bollenbach-Wahl,
• Ralf Braun,
• Rahel Getachew,
• Sabine Hohmann,
• Kwang-Yoon Ko,
• Karoline Kurowski,
• Bernd Laber,
• Rebecca L. Mattison,
• Thomas Müller,
• Anna M. Reingruber,
• Dirk Schmutzler and
• Andrea Svejda

Beilstein J. Org. Chem. 2024, 20, 540–551, doi:10.3762/bjoc.20.46

• synthetic route, which enabled us to introduce a methyl substituent in this position. Likewise, methyl-substituted thiazolo[4,5-b]pyridines 5, 15a, and 15c were synthesized using an optimized Suzuki coupling and served together with compounds 12a–c as key intermediates to explore different reagents and

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

• contrast, only a few examples of fluoranthene backbone preparation by Pd-catalyzed C–H arylation have been reported. Some examples of the preparation of this skeleton by Suzuki coupling followed by intramolecular C–H coupling have been described [18][19][20][21][22][23][24]. In 2017, Metin, Türkmen and co

• intermolecular Suzuki coupling with an intramolecular C–H arylation, it should be possible to access numerous fluoranthene derivatives from commercially available 1,8-dibromobenzene in a single manipulation (Scheme 1d). Here, we describe i) conditions enabling the annulative π-extension of 1,8-dibromonaphthalene

Thienothiophene-based organic light-emitting diode: synthesis, photophysical properties and application

• Recep Isci and
• Turan Ozturk

Beilstein J. Org. Chem. 2023, 19, 1849–1857, doi:10.3762/bjoc.19.137

• 4-bromo-N,N-diphenylaniline (5) with n-butyllithium at −78 °C and addition of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. The Suzuki-coupling reaction of TT 4 with borolane 6 produced the intermediate 7 in 81% yield. The target D–π–A-type fluorophore, DMB-TT-TPA (8), was produced by

Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials

• Jessica Villegas,
• Bryce C. Ball,
• Katelyn M. Shouse,
• Caleb W. VanArragon,
• Ashley N. Wasserman,
• Hannah E. Bhakta,
• Allen G. Oliver,
• Danielle A. Orozco-Nunnelly and
• Jeffrey M. Pruet

Beilstein J. Org. Chem. 2023, 19, 1511–1524, doi:10.3762/bjoc.19.108

• complete decomposition. With the desired naphthylamines in hand, we were able to complete our synthesis of four chelerythrine variants as shown in Scheme 7. After N-formylation providing intermediates 11 and 12 in good yield, a three-step sequence was performed: Suzuki coupling of the aryl bromide with one

Consecutive four-component synthesis of trisubstituted 3-iodoindoles by an alkynylation–cyclization–iodination–alkylation sequence

• Nadia Ledermann,
• Alae-Eddine Moubsit and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2023, 19, 1379–1385, doi:10.3762/bjoc.19.99

• N-iodosuccinimide prior to N-alkylation to give substituted 3-iodoindoles in a concise consecutive four-component fashion in modest to good yields. These target compounds are versatile building blocks for instance for a Suzuki coupling to give 1-alkyl-2,3-diarylindoles that can be of particular

• -dibromoaniline (1c); bwith 4-bromo-2-iodoaniline (1d)). Consecutive double alkynylation–cyclization–iodination–alkylation pseudo-five-component synthesis of 5-phenylethynyl-1,2-disubstituted 3-iodoindole 6. Suzuki coupling of 3-iodoindole 5a with arylboronic acids 7 to give 1,2,3-trisubstituted indoles 8

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

• . Notably, carbonylative amidation of a borylated aryl bromide to 26d proceeded well, where a Pd-catalyzed carbonylative amidation reaction would be plagued by undesired Suzuki coupling. Several secondary cyclic and acyclic amines, as well as primary amines were successfully employed as amine coupling

Construction of hexabenzocoronene-based chiral nanographenes

• Ranran Li,
• Di Wang,
• Shengtao Li and
• Peng An

Beilstein J. Org. Chem. 2023, 19, 736–751, doi:10.3762/bjoc.19.54

• the prefused building block in a 49% yield. Then naphthalene and phenanthrene residues were introduced into compound 33 through Suzuki coupling reaction, the corresponding precursors 34 and 36 were obtained respectively in high yields. The final cyclodehydrogenation using DDQ and TfOH proceeded

Strategies in the synthesis of dibenzo[b,f]heteropines

• David I. H. Maier,
• Barend C. B. Bezuidenhoudt and
• Charlene Marais

Beilstein J. Org. Chem. 2023, 19, 700–718, doi:10.3762/bjoc.19.51

• . through a multicomponent reaction system [57]. The authors provided a series of substituted derivatives through Pd/Rh-catalysed domino coupling. The reaction proceeded via a Suzuki coupling, followed by an in situ Buchwald–Hartwig amination. The authors reported moderate to good yields in a series with

• towards dibenzo[b,f]azepines and other dibenzo[b,f]heteropines, and the functionalisation thereof. Modern metal-catalyzed methods to introduce the C–C bridge include the Heck reaction, the Sonogashira reaction, Suzuki coupling and ring-closing metathesis, whereas Buchwald–Hartwig type reactions and Ullman

• dibenzoazepines 62. Double Buchwald–Hartwig amination towards 10,11-dihydro-5H-dibenzo[b,f]azepine derivatives 71. One-pot Suzuki coupling–Buchwald–Hartwig amination. One-pot Rh/Pd-catalysed synthesis of dihydropyridobenzazepines. A retrosynthetic pathway to dibenzo[b,f]azepines via Mizoroki–Heck reaction. One

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

• substitution for the minimization of 1,3-allylic strain to enable Suzuki coupling for biaryl formation as a single atropisomer. The optimized conditions for this transformation utilize Buchwald’s catalyst (SPhos and Pd-based G2 precatalyst) in conjunction with K3PO4. With DBCOD bearing carboxylic acid handles

Inline purification in continuous flow synthesis – opportunities and challenges

• Jorge García-Lacuna and
• Marcus Baumann

Beilstein J. Org. Chem. 2022, 18, 1720–1740, doi:10.3762/bjoc.18.182

• produced as byproduct in the metathesis reaction. Some subsequent publications include the Pd-complex removal after a Suzuki coupling [126], a Heck catalyst retention with reverse boiling-point-order solvent exchange [127], and a membrane for recovery of the photocatalyst TBADT (tetrabutylammonium

Total synthesis of grayanane natural products

• Nicolas Fay,
• Rémi Blieck,
• Cyrille Kouklovsky and
• Aurélien de la Torre

Beilstein J. Org. Chem. 2022, 18, 1707–1719, doi:10.3762/bjoc.18.181

• diastereoselectivity in 58% on a 3 g scale. Subsequently, vinyl halide 48 was converted to diene 50 by Suzuki coupling with potassium vinyltrifluoroborate (49) in 90% yield (Scheme 8). The C7–C8 bond formation from a bridgehead carbocation was a real challenge to close the 7-membered ring. To achieve this, the

Synthesis of highly substituted fluorenones via metal-free TBHP-promoted oxidative cyclization of 2-(aminomethyl)biphenyls. Application to the total synthesis of nobilone

• Ilya A. P. Jourjine,
• Lukas Zeisel,
• Jürgen Krauß and
• Franz Bracher

Beilstein J. Org. Chem. 2021, 17, 2668–2679, doi:10.3762/bjoc.17.181

• frequently and at various positions in fluorenones from nature. The model cyclization precursors were prepared in two step syntheses by Suzuki coupling [58] of commercially available ortho-substituted areneboronic acids 7 and bromobenzenes 6, 12, and 13 followed by either reductive amination [59] in the case

• aryllithium intermediate. For the synthesis of the benzylamine unit, commercially available nitrile 19 was reacted with NBS to regioselectively introduce a bromo substituent to give bromobenzonitrile 20 in a yield of 51% [65]. Biaryl 21 was constructed via a Suzuki coupling [57] of 18 and 20 in 41% yield. As

Ligand-dependent stereoselective Suzuki–Miyaura cross-coupling reactions of β-enamido triflates

• Tomáš Chvojka,
• Athanasios Markos,
• Svatava Voltrová,
• Radek Pohl and
• Petr Beier

Beilstein J. Org. Chem. 2021, 17, 2657–2662, doi:10.3762/bjoc.17.179

• bond of vinyl (pseudo)halides during the Suzuki coupling have been published [25][26][27][28][29]. Typically, inversion of configuration occurs on substrates containing a double bond in conjugation with an electron-withdrawing group, such as the carbonyl group in enones [27][30]. We hypothesized that

• Information File 1). Subsequently the optimized conditions for preferential formation of 3 were used in the scope study and in all cases, isomeric products 3 formed preferentially (Scheme 2). The highest selectivity in favor to enamide 3 was noted in the Suzuki coupling of vinyl triflate 1d bearing a 2

• -substituted enamides. Substrate scope of the Suzuki coupling leading to enamides 2 and 3. aRatio determined by 19F NMR; byield determined by 19F NMR using PhCF3 as an internal standard; cisolated yield; disolated as a mixture of isomers E/Z = 64:36. Proposed mechanisms for the formed Suzuki coupling retention