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

• %). This cascade involves an initial Suzuki–Miyaura cross-coupling reaction between 1,8-dihalonaphthalenes and heteroarylboronic acids or esters, followed by an intramolecular C–H arylation under the same conditions to yield the final heterocyclic fluoranthene analogues. The method was further employed to

• analogues via a Pd-catalyzed reaction cascade that consists of a Suzuki–Miyaura cross-coupling reaction followed by an intramolecular C–H arylation. These heterocyclic fluoranthene analogues include a variety of acenaphthylene-fused heteroarenes such as thiophene, furan, benzofuran, pyrazole, pyridine and

Novel analogues of a nonnucleoside SARS-CoV-2 RdRp inhibitor as potential antivirotics

• Luca Julianna Tóth,
• Kateřina Krejčová,
• Milan Dejmek,
• Eva Žilecká,
• Blanka Klepetářová,
• Lenka Poštová Slavětínská,
• Evžen Bouřa and
• Radim Nencka

Beilstein J. Org. Chem. 2024, 20, 1029–1036, doi:10.3762/bjoc.20.91

• synthetic strategy leading to pyridones bearing different aryl substituents is described in Scheme 2. During the Suzuki–Miyaura cross-coupling reaction, which introduced the substituents in the C-5 position, the methyl ester protection of the amino acid moiety was also cleaved, leading directly to the final

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

• ]azepine and tetrabromothiophene-S,S-dioxide, followed by oxidative aromatization in the presence DDQ to afford compound 25 in an overall 75% yield. Suzuki−Miyaura cross-coupling reaction of compound 25 with (4-ethylphenyl)boronic acid in the presence of Pd(CH3CN)2Cl2, SPhos, and K3PO4 then furnished the

• nanographenes 96 and 100 using helicene or oxa-helicene as the linkers, respectively [56]. The first π-extension started from the borylated penta-tert-butyl HBC 92. The chemical selective Suzuki−Miyaura cross-coupling reaction between 92 and 93 followed by Scholl oxidation produced compound 94 in an overall 50

Synthesis and investigation on optical and electrochemical properties of 2,4-diaryl-9-chloro-5,6,7,8-tetrahydroacridines

• Najeh Tka,
• Mohamed Adnene Hadj Ayed,
• Mourad Ben Braiek,
• Mahjoub Jabli and
• Peter Langer

Beilstein J. Org. Chem. 2021, 17, 2450–2461, doi:10.3762/bjoc.17.162

• 3,5-dibromoanthranilic acid (1) [61] with cyclohexanone in POCl3 through an adapted reported procedure [62] (Scheme 1). With precursor 2 in hand, we intended to expand the π-conjugation of the tetrahydroacridine core by adding diversely substituted aryl groups using the Suzuki–Miyaura cross-coupling

• reaction [63][64]. As a model reaction, we studied the coupling between 2,4-dibromo-9-chloro-5,6,7,8-tetrahydroacridine (2) and phenylboronic acid (3a). After a thorough optimization using Pd(PPh3)4 as catalyst, toluene as solvent, and K3PO4 as base, the desired bis-arylated product 4a was isolated in up

Synthesis of phenanthridines via a novel photochemically-mediated cyclization and application to the synthesis of triphaeridine

• Songeziwe Ntsimango,
• Kennedy J. Ngwira,
• Moira L. Bode and
• Charles B. de Koning

Beilstein J. Org. Chem. 2021, 17, 2340–2347, doi:10.3762/bjoc.17.152

• –Miyaura cross-coupling reaction of a variety of halogenated methoxybenzene-containing compounds with 2-(formylphenyl)boronic acids in generally good yields [15]. As a next step, the biaryl aldehydes 13a–f were converted into their corresponding oximes 14a–f in good yields as a mixture of (E) and (Z

• substituents in a range of positions. In all cases at least one methoxy substituent was positioned ortho- to the biaryl axis. The other aromatic ring had to contain an oxime ester, which would form an iminyl electron donor, as shown in Scheme 2. As illustrated substrates 13a–f were accessed using the Suzuki

Double-headed nucleosides: Synthesis and applications

• Vineet Verma,
• Jyotirmoy Maity,
• Vipin K. Maikhuri,
• Ritika Sharma,
• Himal K. Ganguly and
• Ashok K. Prasad

Beilstein J. Org. Chem. 2021, 17, 1392–1439, doi:10.3762/bjoc.17.98

Design, synthesis and photophysical properties of novel star-shaped truxene-based heterocycles utilizing ring-closing metathesis, Clauson–Kaas, Van Leusen and Ullmann-type reactions as key tools

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2021, 17, 1374–1384, doi:10.3762/bjoc.17.96

• be inspected from Scheme 7, our journey in this regard stem from the iodination of 2 using H5IO6/I2/H2SO4 in acetic acid–water solvent system to afford the desired triiodotruxene derivative 22 in 50% yield. Furthermore, Suzuki–Miyaura cross-coupling reaction of 22 with 4-formylphenylboronic acid (23

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

• Suzuki–Miyaura cross-coupling reaction of bromosumanene 82 under microwave reaction conditions. Whereas another route involves the Ni-catalyzed aryl–aryl homo-coupling between the two molecules of iodosumanene 79 [51][52]. Moreover, the bissumanenyl 92, which is thought to be chiral because of the two

• , very few reports could be found for selective functionalization at the peripheral carbons because of difficulties arose during their synthesis. In this regard, Toda et al. in 2017 have successfully synthesized 2,3,5,6,8,9-hexaarylsumanene derivatives 95a–h utilizing a Suzuki–Miyaura cross-coupling

• reaction as the critical step [54]. Towards this goal, they started with the hexabromination of sumanene using bromine and iron powder in nitrobenzene to provide the desired compound 94 in 61% yield. Having the bromosumanene 94 in hand, it was then subjected to the Suzuki coupling with several arylboronic

One-pot and metal-free synthesis of 3-arylated-4-nitrophenols via polyfunctionalized cyclohexanones from β-nitrostyrenes

• Haruyasu Asahara,
• Minami Hiraishi and
• Nagatoshi Nishiwaki

Beilstein J. Org. Chem. 2020, 16, 1830–1836, doi:10.3762/bjoc.16.150

• group hinder the electrophilic modification at the 3-position. Generally, the aryl group is introduced by a Suzuki–Miyaura cross-coupling reaction [4][5], for which 3-bromo-4-nitrophenol must be prepared by the nitration of 3-bromophenol [6][7]. An alternative approach is the nitration of 3-arylphenol

Direct borylation of terrylene and quaterrylene

• Haruka Kano,
• Keiji Uehara,
• Kyohei Matsuo,
• Hironobu Hayashi,
• Hiroko Yamada and
• Naoki Aratani

Beilstein J. Org. Chem. 2020, 16, 621–627, doi:10.3762/bjoc.16.58

• hinderance of Bpin moieties. Finally, to demonstrate the utility of the borylated oligorylenes, the Suzuki–Miyaura cross-coupling reaction of TB4 under the standard conditions was performed (Scheme 3). Coupling of TB4 and 2-bromomesitylene with Pd(PPh3)4, Cs2CO3 and CsF in a mixture of toluene/DMF furnished

• -dioxaborolan-2-yl. Synthesis of 2,5,12,15-tetrakis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quaterrylene (QB4): (a) (Bpin)2 (12 equiv), [Ir(OMe)cod]2 (20 mol %), di-tert-butylbipyridyl (40 mol %), 1,4-dioxane, at 105 °C, 38 h, yield 0.4%. Suzuki–Miyaura cross-coupling reaction of TB4 with 2-bromomesitylene

Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C–F···H–C bonds

• Vuyisa Mzozoyana,
• Fanie R. van Heerden and
• Craig Grimmer

Beilstein J. Org. Chem. 2020, 16, 190–199, doi:10.3762/bjoc.16.22

• cross-coupling reaction [17], Negishi cross-coupling reaction [18] and Wittig reaction [17]. The concept of the incorporation of fluorine into organic molecules has gained much interest since Fried and Sabo reported the improvement of the therapeutic index of cortisol by the incorporation of a fluorine

• , numerous methods for the synthesis of these compounds have been developed, examples are the Pechmann condensation [10][11], Stille coupling reaction [12], Knoevenagel condensation [13], Heck coupling reaction [14], Kostanecki reaction, Baylis–Hillman reaction [15], Michael reaction [16], Suzuki–Miyaura

An improved, scalable synthesis of Notum inhibitor LP-922056 using 1-chloro-1,2-benziodoxol-3-one as a superior electrophilic chlorinating agent

• Nicky J. Willis,
• Elliott D. Bayle,
• George Papageorgiou,
• David Steadman,
• Benjamin N. Atkinson,
• William Mahy and
• Paul V. Fish

Beilstein J. Org. Chem. 2019, 15, 2790–2797, doi:10.3762/bjoc.15.271

• biology of Notum and build target validation to underpin new drug discovery programs. Results: An improved, scalable synthesis of 1 is reported. Key modifications include: (1) the introduction of the C7-cyclopropyl group was most effectively achieved with a Suzuki–Miyaura cross-coupling reaction with MIDA

• group was most effectively achieved with a Suzuki–Miyaura cross-coupling reaction with MIDA-boronate 11 (5 → 6); and (2) C6 chlorination was performed with 1-chloro-1,2-benziodoxol-3-one (12) (6 → 7) as a mild selective electrophilic chlorination agent. 4-Chlorothieno[3,2-d]pyrimidine (3) was either

• modifications include: (1) the introduction of the C7-cyclopropyl group was most effectively achieved with a Suzuki–Miyaura cross-coupling reaction with MIDA-boronate 11 (5 → 6); and (2) C6 chlorination was performed with 1-chloro-1,2-benziodoxol-3-one (12) (6 → 7) as a mild selective electrophilic chlorination

A new approach to silicon rhodamines by Suzuki–Miyaura coupling – scope and limitations

• Thines Kanagasundaram,
• Antje Timmermann,
• Carsten S. Kramer and
• Klaus Kopka

Beilstein J. Org. Chem. 2019, 15, 2569–2576, doi:10.3762/bjoc.15.250

• the Suzuki–Miyaura cross-coupling reaction gave access to silicon rhodamines with neutral (hetero)aromatic xanthene substituents (phenyl: 67%, respectively 73% brsm; thienyl: 91%) (even though the term ‘dihydrosilaanthracene’ is correct to name the Si-anthracene moiety, the term ‘Si-xanthene’ is

Self-assembled coordination thioether silver(I) macrocyclic complexes for homogeneous catalysis

• Zhen Cao,
• Aline Lacoudre,
• Cybille Rossy and
• Brigitte Bibal

Beilstein J. Org. Chem. 2019, 15, 2465–2472, doi:10.3762/bjoc.15.239

• reactions of alkynes. Results and Discussion Synthesis of silver(I) complexes Ligand 1 was synthesized in one step, from commercially available 9,10-dibromoanthracene and 2-(methylthio)phenylboronic acid, using a Suzuki–Miyaura cross-coupling reaction. Notably, the yield was low (26%) [55], and the X-ray

Solid-phase synthesis of biaryl bicyclic peptides containing a 3-aryltyrosine or a 4-arylphenylalanine moiety

• Iteng Ng-Choi,
• Àngel Oliveras,
• Lidia Feliu and
• Marta Planas

Beilstein J. Org. Chem. 2019, 15, 761–768, doi:10.3762/bjoc.15.72

• cross-coupling reaction [15][16][17][18][19] or via a Pd-catalyzed C–H activation reaction [20][21]. We have used the former reaction for the solid-phase preparation of biaryl cyclic peptides bearing a Phe-Phe, a Phe-Tyr or a Tyr-Tyr linkage [22][23]. Our approach involved the synthesis of the linear

• positively charged groups. Due to these structural properties, biaryl cyclic peptides have a great potential to meet the ever-increasing expectations of new drugs. However, their synthesis is viewed as very challenging. The formation of biaryl bonds in peptides has been performed through a Suzuki–Miyaura

Some mechanistic aspects regarding the Suzuki–Miyaura reaction between selected ortho-substituted phenylboronic acids and 3,4,5-tribromo-2,6-dimethylpyridine

• Piotr Pomarański,
• Piotr Roszkowski,
• Jan K. Maurin,
• Armand Budzianowski and
• Zbigniew Czarnocki

Beilstein J. Org. Chem. 2018, 14, 2384–2393, doi:10.3762/bjoc.14.214

• atropselective Suzuki–Miyaura cross-coupling reaction on 3,4,5-tribromo-2,6-dimethylpyridine was studied. Results: Reactions with various amounts of ortho-substituted phenylboronic acids with 3,4,5-tribromo-2,6-dimethylpyridine gave a series of mono- di- and triarylpyridine derivatives which allowed to draw

• [10][11][12][13]. In recent years, many successful attempts to regioselective [14][15][16][17], chemoselective [18][19][20][21] or atropselective [1][22][23][24][25][26] synthesis of biaryls were presented, often taking advantage of the popular and useful Suzuki–Miyaura cross-coupling reaction

• chloropyridines, significantly less-reactive in palladium cross-coupling reaction, were used as substrates allowing the formation of the desired products. Another regioselective Suzuki–Miyaura cross-coupling reaction on 3’,5’-dibromopyridinium N-(2’-azinyl)aminides afforded a series of 3-aryl(or heteroaryl)-5

Water-soluble SNS cationic palladium(II) complexes and their Suzuki–Miyaura cross-coupling reactions in aqueous medium

• Alphonse Fiebor,
• Richard Tia,
• Banothile C. E. Makhubela and
• Henok H. Kinfe

Beilstein J. Org. Chem. 2018, 14, 1859–1870, doi:10.3762/bjoc.14.160

• reaction involving 4-bromoanisole and Pd(II) catalyst precursor 17d. The change in energy for 17d was calculated by computing it in kcal/mol as a cation at 298.15 K and 1 atm. Reusability of pincer complex 17d as a catalyst for the Suzuki–Miyaura cross coupling reaction. Synthesis of pincer ligands 19a–d

• of the Suzuki–Miyaura cross coupling reaction of 4-bromoanisole (21a) and phenylboronic acid (22a). Results from the Suzuki–Miyaura cross-coupling reactions of various aryl bromides and boronic acids using pincer complex 17d as catalyst.a Supporting Information Supporting Information File 391

Recent applications of chiral calixarenes in asymmetric catalysis

• Mustafa Durmaz,
• Erkan Halay and
• Selahattin Bozkurt

Beilstein J. Org. Chem. 2018, 14, 1389–1412, doi:10.3762/bjoc.14.117

• were tested in the palladium-catalyzed asymmetric Suzuki–Miyaura cross-coupling reaction for the first time in this study (Scheme 8). In order to see whether the calixarene backbone can effect the the coupling reaction between 1-naphthaleneboronic acid (30) and 1-bromo-2-methylnaphthalene (31), their

[3 + 2]-Cycloaddition reaction of sydnones with alkynes

• Veronika Hladíková,
• Jiří Váňa and
• Jiří Hanusek

Beilstein J. Org. Chem. 2018, 14, 1317–1348, doi:10.3762/bjoc.14.113

• group can be easily substituted by an aryl group using a Suzuki–Miyaura cross-coupling reaction. In those cases when a trimethylsilyl group (R4) is also present, it can be removed by TBAF-mediated protodesilylation to give a 1,4,5-trisubstituted pyrazole. It is worth noting that the parent 4,4,5,5

Heterogeneous Pd catalysts as emulsifiers in Pickering emulsions for integrated multistep synthesis in flow chemistry

• Katharina Hiebler,
• Georg J. Lichtenegger,
• Manuel C. Maier,
• Eun Sung Park,
• Renie Gonzales-Groom,
• Bernard P. Binks and
• Heidrun Gruber-Woelfler

Beilstein J. Org. Chem. 2018, 14, 648–658, doi:10.3762/bjoc.14.52

• ) [31][32][33][34][35]. A preliminary scheme of the planned synthetic route is shown in Figure 1. As can be seen, the key step of our processes is the formation of the biaryl unit via a Suzuki–Miyaura cross-coupling reaction. To provide solid Pd catalysts with a high potential for the planned approaches

Synthesis and spectroscopic properties of β-meso directly linked porphyrin–corrole hybrid compounds

• Baris Temelli and
• Hilal Kalkan

Beilstein J. Org. Chem. 2018, 14, 187–193, doi:10.3762/bjoc.14.13

• -porphyrin, β-corrole-linked hybrid structure described a Suzuki–Miyaura cross-coupling reaction between a β-borylated corrole and meso-bromoporphyrins (Scheme 1D) [37]. Recently, we have successfully synthesized meso–meso and β-meso-linked imine-bridged porphyrin–corrole conjugates and investigated

The chemistry and biology of mycolactones

• Matthias Gehringer and
• Karl-Heinz Altmann

Beilstein J. Org. Chem. 2017, 13, 1596–1660, doi:10.3762/bjoc.13.159

Nitration of 5,11-dihydroindolo[3,2-b]carbazoles and synthetic applications of their nitro-substituted derivatives

• Roman A. Irgashev,
• Nikita A. Kazin,
• Gennady L. Rusinov and
• Valery N. Charushin

Beilstein J. Org. Chem. 2017, 13, 1396–1406, doi:10.3762/bjoc.13.136

• performed by using the Suzuki–Miyaura cross-coupling reaction with phenylboronic acid under Pd catalysis (Scheme 5). The location of the formyl group and bromine atoms in ICZ derivatives 12 and 13 has been established by X-ray crystallography analysis, performed for single crystals of 12b and 13b (Figure 5

Total synthesis of elansolids B1 and B2

• Liang-Liang Wang and
• Andreas Kirschning

Beilstein J. Org. Chem. 2017, 13, 1280–1287, doi:10.3762/bjoc.13.124

• . Results and Discussion The improved synthesis utilizes the Suzuki–Miyaura cross-coupling reaction to merge the western fragment derived from ketone 9 with the newly designed eastern building block 13. This fragment was obtained in very good yield from vinyl iodide 12 [9] by a Stille protocol using doubly

• )-configured triene units are ideally be constructed, clearly demonstrating that enediynes are less preferred precursors for such structural elements. It has to be noted that there is precedence in the literature for the use of the Suzuki–Miyaura cross-coupling reaction as key step to assemble differently

A convenient route to symmetrically and unsymmetrically substituted 3,5-diaryl-2,4,6-trimethylpyridines via Suzuki–Miyaura cross-coupling reaction

• Dariusz Błachut,
• Joanna Szawkało and
• Zbigniew Czarnocki

Beilstein J. Org. Chem. 2016, 12, 835–845, doi:10.3762/bjoc.12.82

• convenient synthesis of symmetrically and unsymmetrically substituted 3,5-diaryl-2,4,6-trimethylpyridines via Suzuki–Miyaura cross-coupling reaction. Several diarylpyridines with mixed aryl rings were produced by sequential two-step Suzuki cross-coupling reaction with separation of intermediary 3-aryl-5