Search results

Search for "cross-coupling reactions" in Full Text gives 282 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Synthesis of benzo[f]quinazoline-1,3(2H,4H)-diones

  • Ruben Manuel Figueira de Abreu,
  • Peter Ehlers and
  • Peter Langer

Beilstein J. Org. Chem. 2024, 20, 2708–2719, doi:10.3762/bjoc.20.228

Graphical Abstract
  • and Suzuki–Miyaura cross-coupling reactions followed by Brønsted acid-mediated cycloisomerisation. The developed methodology tolerates various functional groups and leads to moderate up to quantitative yields of the final products. The impact of different functional groups on the optical properties
  • of palladium-catalysed Sonogashira–Hagihara and Suzuki–Miyaura cross-coupling reactions (Scheme 1). The final cyclisation step is accomplished by an acid-mediated cycloisomerisation. The synthesis of starting materials 4 was carried out by our previously reported protocol [65]. While compounds 4a–f
  • known which allow for an individual introduction of substituents at both positions [37][38][51][52][53][54][55][56][57][58][59][60][61]. In our previous work, we developed a new method which enables both positions to be independently functionalised by Sonogashira- and Suzuki–Miyaura cross-coupling
PDF
Album
Supp Info
Full Research Paper
Published 28 Oct 2024

Synthesis of fluoroalkenes and fluoroenynes via cross-coupling reactions using novel multihalogenated vinyl ethers

  • Yukiko Karuo,
  • Keita Hirata,
  • Atsushi Tarui,
  • Kazuyuki Sato,
  • Kentaro Kawai and
  • Masaaki Omote

Beilstein J. Org. Chem. 2024, 20, 2691–2703, doi:10.3762/bjoc.20.226

Graphical Abstract
  • fluoroenynes via Suzuki–Miyaura and Sonogashira cross-coupling reactions using novel multihalogenated fluorovinyl ethers, which are easily prepared from the reaction between phenols and 2-bromo-2-chloro-1,1,1-trifluoroethane (halothane). These reactions make use of the unique structure of multihalogenated
  • fluorovinyl ethers, which contains a reactive bromine atom, to afford a series of fluoroalkenes and fluoroenynes in moderate to high yields. Keywords: fluoroalkenes; fluoroenynes; multihalogenated vinyl ethers; Suzuki–Miyaura cross-coupling reactions; Sonogashira cross-coupling reactions; Introduction
  • chlorine atoms as reported by Hosoya and Niwa et al. In this study, we investigated the synthesis of fluoroalkenes 2 or fluoroenynes 3 by Suzuki–Miyaura or Sonogashira cross-couplings with a key building block 1 (Scheme 1D). Results and Discussion Optimization of the conditions of cross-coupling reactions
PDF
Album
Supp Info
Full Research Paper
Published 24 Oct 2024

Transition-metal-free synthesis of arylboronates via thermal generation of aryl radicals from triarylbismuthines in air

  • Yuki Yamamoto,
  • Yuki Konakazawa,
  • Kohsuke Fujiwara and
  • Akiya Ogawa

Beilstein J. Org. Chem. 2024, 20, 2577–2584, doi:10.3762/bjoc.20.216

Graphical Abstract
  • are one of the fundamental aryl compounds in organic synthesis, especially in cross-coupling reactions [1][2][3][4][5][6][7][8][9], and their applications are widespread, including dye synthesis, pharmaceutical and agrochemical synthesis, and industrial manufacturing [10][11]. In recent years, a
PDF
Album
Supp Info
Full Research Paper
Published 11 Oct 2024

A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis

  • Nian Li,
  • Ruzal Sitdikov,
  • Ajit Prabhakar Kale,
  • Joost Steverlynck,
  • Bo Li and
  • Magnus Rueping

Beilstein J. Org. Chem. 2024, 20, 2500–2566, doi:10.3762/bjoc.20.214

Graphical Abstract
  • cathodic reduction and to prevent the reoxidation of the reduced SO2 at the anode, a divided cell setup is required (Scheme 12). C–H bond halogenation: Aryl and alkyl halides are important synthetic building blocks for cross-coupling reactions as well as bioactive molecules with applications in
PDF
Album
Review
Published 09 Oct 2024

Generation of alkyl and acyl radicals by visible-light photoredox catalysis: direct activation of C–O bonds in organic transformations

  • Mithu Roy,
  • Bitan Sardar,
  • Itu Mallick and
  • Dipankar Srimani

Beilstein J. Org. Chem. 2024, 20, 1348–1375, doi:10.3762/bjoc.20.119

Graphical Abstract
  • –halogen bond formation, as well as C–H functionalization [27]. Some notable examples include C–H arylation, various cross-coupling reactions, oxidative coupling, and photocatalytic radical reactions. The advantages of visible-light-induced photoredox catalysis are due to the ability to utilize visible
  • nickel-catalyzed cross-coupling reactions with aryl halides to deliver the desired cross-coupled products. Interestingly, in absence of any xanthate, sec-butyl radicals underwent cross-coupling reactions with aryl halides to form sec-butyl arenes, whereas in the presence of xanthate, no undesired sec
  • -butyl arenes were generated. This underpinned the formation of sec-butyl radicals in the system that rapidly reacted with O-benzyl xanthates before participating in the nickel-catalyzed cross-coupling reactions. Precatalyst [Ni(dtbbpy)(H2O)4]Cl2 (50) and photosensitizer [Ir(dF(CF3)ppy)2(bpy)]PF6 (49
PDF
Album
Review
Published 14 Jun 2024

Synthesis and optical properties of bis- and tris-alkynyl-2-trifluoromethylquinolines

  • Stefan Jopp,
  • Franziska Spruner von Mertz,
  • Peter Ehlers,
  • Alexander Villinger and
  • Peter Langer

Beilstein J. Org. Chem. 2024, 20, 1246–1255, doi:10.3762/bjoc.20.107

Graphical Abstract
  • ][23], dyes, preservatives and as ligands in complex chemistry [24][25][26][27]. In the context of our interest in the application of cross-coupling reactions to polyhalogenated heterocycles [28][29][30][31], we studied Sonogashira reactions of brominated 2-trifluoromethylquinolines. The optical
  • cross-coupling reactions of various acetylenes containing electron-rich and electron-withdrawing functional groups, like methoxy or cyano, as well as thienyl and cyclopropyl groups. In general, all products were achieved in very good yields, ranging from 71 to 99%. Only product 6h, containing a TMS
PDF
Album
Supp Info
Full Research Paper
Published 29 May 2024

Manganese-catalyzed C–C and C–N bond formation with alcohols via borrowing hydrogen or hydrogen auto-transfer

  • Mohd Farhan Ansari,
  • Atul Kumar Maurya,
  • Abhishek Kumar and
  • Saravanakumar Elangovan

Beilstein J. Org. Chem. 2024, 20, 1111–1166, doi:10.3762/bjoc.20.98

Graphical Abstract
  • importance in organic synthesis and is widely used in the pharmaceutical and other chemical industries. Palladium-catalyzed cross-coupling reactions are one of the compelling methods for building C–C and C–N bonds [1][2]. However, using organohalide reagents and harsh reaction conditions in this process
  • are of substantial importance for the fine chemical industry, pharmaceuticals, agrochemicals, dyes, and natural products [25]. The synthesis of amine derivatives can be accomplished using many powerful techniques, including Buchwald–Hartwig and Ullmann cross-coupling reactions, hydroamination
  • , hydroaminomethylation, reduction of nitriles and nitro compounds or through reductive amination of carbonyl derivatives [26][27][28][29][30]. However, for example, cross-coupling reactions with alkyl or aryl halides generate considerable amounts of waste (Scheme 2A). Even though many different approaches exist for
PDF
Album
Review
Published 21 May 2024

(Bio)isosteres of ortho- and meta-substituted benzenes

  • H. Erik Diepers and
  • Johannes C. L. Walker

Beilstein J. Org. Chem. 2024, 20, 859–890, doi:10.3762/bjoc.20.78

Graphical Abstract
  • esterification of alcohol (±)-5 gave redox active ester (±)-6, which was itself shown to be a suitable substrate for nickel-catalysed decarboxylative cross coupling reactions to aryl-substituted BCPs (±)-7. Oxidation of alcohol (±)-8 gave acid (±)-9 which yielded amine (±)-10 after a Curtius rearrangement
  • decarboxylation then yields 1,2-cubane 88. This synthesis reduced the number of synthetic steps from eight, in the previously known patented synthesis from 2007 [54], to four. MacMillan and co-workers also developed a number of decarboxylative cross-coupling reactions to allow access to an even wider range of 1,2
  • conditions in the transformation of alcohol 153 to aldehyde 154. All of these transformations could be performed without reduction in diastereomeric ratio. Additionally, the authors showed that acid 152 can undergo nickel-catalysed decarboxylative cross coupling reactions via redox active ester 156 to afford
PDF
Album
Review
Published 19 Apr 2024

Ortho-ester-substituted diaryliodonium salts enabled regioselective arylocyclization of naphthols toward 3,4-benzocoumarins

  • Ke Jiang,
  • Cheng Pan,
  • Limin Wang,
  • Hao-Yang Wang and
  • Jianwei Han

Beilstein J. Org. Chem. 2024, 20, 841–851, doi:10.3762/bjoc.20.76

Graphical Abstract
  • for the synthesis of functional materials via cross-coupling reactions. Next, we extended our investigation to 1-naphthol in this reaction, and found that the arylation of 1-naphthol was achieved selectively at the C-2 position. The cascade cyclization resulted in the corresponding products 3an and
PDF
Album
Supp Info
Letter
Published 18 Apr 2024

Mechanisms for radical reactions initiating from N-hydroxyphthalimide esters

  • Carlos R. Azpilcueta-Nicolas and
  • Jean-Philip Lumb

Beilstein J. Org. Chem. 2024, 20, 346–378, doi:10.3762/bjoc.20.35

Graphical Abstract
  • of parameters with which to control reactivity. In this perspective, we provide an overview of the different mechanisms for radical reactions involving NHPI esters, with an emphasis on recent applications in radical additions, cyclizations and decarboxylative cross-coupling reactions. Within these
  • years and in the past, they were perceived as fleeting reaction intermediates. Recent progress in photoredox catalysis [6][7][8], electrochemistry [9][10], and the use of transition-metal (TM) catalysts in radical cross-coupling reactions [11] have dramatically expanded the use of radicals in synthesis
PDF
Album
Perspective
Published 21 Feb 2024

Nucleophilic functionalization of thianthrenium salts under basic conditions

  • Xinting Fan,
  • Duo Zhang,
  • Xiangchuan Xiu,
  • Bin Xu,
  • Yu Yuan,
  • Feng Chen and
  • Pan Gao

Beilstein J. Org. Chem. 2024, 20, 257–263, doi:10.3762/bjoc.20.26

Graphical Abstract
  • the resulting products (3ah–aj) can also be obtained with high efficiency. This underscores the viability of integrating this metal-free thioetherification method with other traditional cross-coupling reactions. Sterically hindered ortho-disubstituted thiophenol 2k is also compatible with this
PDF
Album
Supp Info
Full Research Paper
Published 08 Feb 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

Graphical Abstract
  • their biological activity and potential applications, continuous efforts have been dedicated to the synthesis of DHPI derivatives. Various synthetic strategies have been explored (Scheme 1), including transition-metal-catalyzed cross-coupling reactions [8][9][10], annulation reaction of carbenoids [11
PDF
Album
Supp Info
Full Research Paper
Published 19 Jan 2024

Biphenylene-containing polycyclic conjugated compounds

  • Cagatay Dengiz

Beilstein J. Org. Chem. 2023, 19, 1895–1911, doi:10.3762/bjoc.19.141

Graphical Abstract
  • through Sonogashira cross-coupling reactions with alkynes featuring different protecting groups such as TIPS, TES, and TIBS. Scheme 7 illustrates the derivatization process using one of the chosen examples, specifically the TIPS group. Accordingly, the cross-coupling products 33a–c were obtained in yields
PDF
Album
Review
Published 13 Dec 2023

Recent advancements in iodide/phosphine-mediated photoredox radical reactions

  • Tinglan Liu,
  • Yu Zhou,
  • Junhong Tang and
  • Chengming Wang

Beilstein J. Org. Chem. 2023, 19, 1785–1803, doi:10.3762/bjoc.19.131

Graphical Abstract
  • the photoredox cross-coupling reactions discussed above. A recent elegant study conducted by Chen and colleagues introduced a straightforward method that directly employed sodium iodide for photoinduced deaminative alkenylation processes [11]. This method enabled the synthesis of β,γ-unsaturated
  • radicals for alkenylation, was primarily facilitated by the electrostatic interaction between NaI and Katritzky salts 7. This innovative approach not only expanded the scope of photoredox cross-coupling reactions but also offered valuable insights into the role of NaI in facilitating these transformations
  • -anion catalysis under visible light irradiation, as depicted in Scheme 9. Subsequent investigations revealed that redox-active esters 3 and Katritzky salts 15 derived from amino acids could be effectively employed in decarboxylative/deaminative cross-coupling reactions [15]. These reactions enabled the
PDF
Album
Review
Published 22 Nov 2023

Radical chemistry in polymer science: an overview and recent advances

  • Zixiao Wang,
  • Feichen Cui,
  • Yang Sui and
  • Jiajun Yan

Beilstein J. Org. Chem. 2023, 19, 1580–1603, doi:10.3762/bjoc.19.116

Graphical Abstract
  • to produce conductive polymers (Scheme 9B) [76]. Nowadays, most conductive polymers are prepared via metal-catalyzed cross-coupling reactions [77]. However, radical polymerization is also an effective way to synthesize conductive polymers at a relatively low cost. Niemi et al. [78] used FeCl3 as
PDF
Album
Review
Published 18 Oct 2023

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

Graphical Abstract
  • berberine variants none are as easily modulated to rapidly install substituent diversity [31][43][44][45][46][47][48]. The method deemed most amenable to varying substituents involves substituted 2-bromo-1-aminonaphthalenes which are used in subsequent palladium cross-coupling reactions [45]. As such, our
PDF
Album
Supp Info
Full Research Paper
Published 29 Sep 2023

N-Sulfenylsuccinimide/phthalimide: an alternative sulfenylating reagent in organic transformations

  • Fatemeh Doraghi,
  • Seyedeh Pegah Aledavoud,
  • Mehdi Ghanbarlou,
  • Bagher Larijani and
  • Mohammad Mahdavi

Beilstein J. Org. Chem. 2023, 19, 1471–1502, doi:10.3762/bjoc.19.106

Graphical Abstract
  • functional materials and indispensable synthetic intermediates in drug discovery [31][32][33]. Because of their value, constructing C–S bonds has attracted significant attention via metal-catalyzed cross-coupling reactions and metal-free C–S bond formation [34][35][36][37]. Direct sulfenylation of the C–H
PDF
Album
Review
Published 27 Sep 2023

Visible-light-induced nickel-catalyzed α-hydroxytrifluoroethylation of alkyl carboxylic acids: Access to trifluoromethyl alkyl acyloins

  • Feng Chen,
  • Xiu-Hua Xu,
  • Zeng-Hao Chen,
  • Yue Chen and
  • Feng-Ling Qing

Beilstein J. Org. Chem. 2023, 19, 1372–1378, doi:10.3762/bjoc.19.98

Graphical Abstract
  • reaction scope and development of related enantioselective photoinduced nickel-catalyzed radical cross-coupling reactions are currently underway in our laboratory. Experimental General procedure for the visible-light-induced nickel-catalyzed cross coupling of alkyl carboxylic acids with N
PDF
Album
Supp Info
Full Research Paper
Published 11 Sep 2023

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

Graphical Abstract
  • become a major strategy for ether functionalization. This review covers C–H/C–H cross-coupling reactions of ether derivatives with various C–H bond substrates via non-noble metal catalysts (Fe, Cu, Co, Mn, Ni, Zn, Y, Sc, In, Ag). We discuss advances achieved in these CDC reactions and hope to attract
PDF
Album
Review
Published 06 Sep 2023

Synthesis of aliphatic nitriles from cyclobutanone oxime mediated by sulfuryl fluoride (SO2F2)

  • Xian-Lin Chen and
  • Hua-Li Qin

Beilstein J. Org. Chem. 2023, 19, 901–908, doi:10.3762/bjoc.19.68

Graphical Abstract
  • of novel synthetic methods and strategies toward nitrile group construction continues to be a focus for synthetic chemists. The cross-coupling reactions of C–C bonds catalyzed by transition-metal complexes play a crucial role in modern organic synthesis, as they make it feasible to synthesize complex
PDF
Album
Supp Info
Letter
Published 22 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

Graphical Abstract
  • pyridines with simple alkenes 96, leading to the C3-alkenylated products 97 (Scheme 19). The reaction was based on the previous reports of using of the MPAA ligands in the Pd-catalyzed oxidative cross-coupling reactions discovered by Yu et al. [87]. When 2-methoxypyridine was screened, the reaction resulted
PDF
Album
Review
Published 12 Jun 2023

Enolates ambushed – asymmetric tandem conjugate addition and subsequent enolate trapping with conventional and less traditional electrophiles

  • Péter Kisszékelyi and
  • Radovan Šebesta

Beilstein J. Org. Chem. 2023, 19, 593–634, doi:10.3762/bjoc.19.44

Graphical Abstract
  • highly beneficial scaffold which was successfully involved in diastereoselective Ni/photoredox dual-catalyzed cross-coupling reactions. Furthermore, rather than the stereoselective protonation, they have also demonstrated the successful trapping of the Cu enolate with benzaldehyde (Scheme 45B). This
PDF
Album
Review
Published 04 May 2023

Total synthesis of insect sex pheromones: recent improvements based on iron-mediated cross-coupling chemistry

  • Eric Gayon,
  • Guillaume Lefèvre,
  • Olivier Guerret,
  • Adrien Tintar and
  • Pablo Chourreu

Beilstein J. Org. Chem. 2023, 19, 158–166, doi:10.3762/bjoc.19.15

Graphical Abstract
  • cross-coupling field. Discussion The quest for non-toxic and efficient additives for iron-mediated cross-coupling reactions Co-solvents used as NMP surrogates In spite of the very good yields and soft conditions provided by Cahiez’ method (Scheme 2b), a major drawback of the latter is the requirement of
  • quest for suitable additives as surrogates of NMP. Szostak and Bisz reported in 2019 that N-methyl-ε-caprolactame (NMCPL) could be used as an alternative solvent, and sp3–sp2 cross-coupling reactions proceeding with good to excellent yields were reported. Alkyl Grignard reagents could thus be used in
  • pheromones involving a key alkyl–alkenyl linkage introduction by iron-catalyzed cross-coupling reactions of α,ω-difunctionalized alkyl Grignard reagents with stereochemically pure dienyl phosphates were successfully performed at higher scales, in order to be successfully implemented in industrial processes
PDF
Album
Perspective
Published 14 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

Graphical Abstract
  • °C and 0 °C, temperatures at which these organometallic reagents are also reported to be quite stable. The zincated dithiins can also be prepared by transmetalation of the magnesiated dithiins at −30 °C, and these organozinc reagents can then be used in room temperature Pd-catalyzed cross-coupling
  • 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 Friedel–Crafts-type pathway onto the released aldehyde moiety
PDF
Album
Review
Published 02 Feb 2023

Practical synthesis of isocoumarins via Rh(III)-catalyzed C–H activation/annulation cascade

  • Qian-Ci Gao,
  • Yi-Fei Li,
  • Jun Xuan and
  • Xiao-Qiang Hu

Beilstein J. Org. Chem. 2023, 19, 100–106, doi:10.3762/bjoc.19.10

Graphical Abstract
  • , delivering a variety of structurally diverse isocoumarins in an efficient manner (3aa–qa, 43–82%). It is worth mentioning that the tolerance of halogen substituents (Cl, Br and I) may open up a new opportunity for further transition-metal-catalyzed cross-coupling reactions. Sensitive groups, such as ester
  • , the reaction of the isocoumarin 3ia with p-toluenesulfonyl hydrazide proceeded smoothly to deliver hydrazone 5 in 66% yield (Scheme 4b, right). Of note, oxime and hydrazone compounds are versatile synthetic building blocks, which have been widely applied in transition-metal-catalyzed cross-coupling
  • reactions and radical transformations [36][37][38]. Based on the literature precedents [27] and our previous work [33][34][35], a mechanism for this Rh-catalyzed C–H activation/annulation reaction was proposed and depicted in Scheme 5. In the presence of AgSbF6, dimeric [Cp*RhCl2]2 transforms into the
PDF
Album
Supp Info
Letter
Published 30 Jan 2023
Other Beilstein-Institut Open Science Activities