Chitosan-supported CuI-catalyzed cascade reaction of 2-halobenzoic acids and amidines for the synthesis of quinazolinones

• Xuhong Zhao,
• Weishuang Li,
• Mengli Yang,
• Bojie Li,
• Yaoyao Zhang,
• Lizhen Huang and
• Lei Zhu

Beilstein J. Org. Chem. 2025, 21, 839–844, doi:10.3762/bjoc.21.67

• under optimized conditions (Scheme 4a). The recyclability of heterogeneous catalysts is a critical factor in assessing their practical utility in transition metal-catalyzed reactions. Therefore, the recyclability of CS@CuI was evaluated in the reaction of 2-iodobenzoic acid (1a) with 2a, as illustrated

Regioselective formal hydrocyanation of allenes: synthesis of β,γ-unsaturated nitriles with α-all-carbon quaternary centers

• Seeun Lim,
• Teresa Kim and
• Yunmi Lee

Beilstein J. Org. Chem. 2025, 21, 800–806, doi:10.3762/bjoc.21.63

• -system configuration promotes selective functionalization, enabling the synthesis of various complex products through a single transformation [17][18][19]. Therefore, allenes have become versatile intermediates in numerous transition-metal-catalyzed reactions [20][21]. Despite extensive studies on the

Recent advances in organocatalytic atroposelective reactions

• Henrich Szabados and
• Radovan Šebesta

Beilstein J. Org. Chem. 2025, 21, 55–121, doi:10.3762/bjoc.21.6

• purities, solid yields and very good diastereomeric ratios. The hydroxy group present in products 156 and 158 could be transformed to provide axially chiral phosphines that could be utilized as chiral ligands in transition-metal-catalyzed reactions. Testing both substrates 156 and 158 for conformational

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

• variety of transition-metal-catalyzed reactions and photoredox reactions using arylboronates as aryl sources have been energetically investigated for the construction of carbon–carbon or carbon–heteroatom bonds [12][13][14][15]. The preparation of arylboronates often requires pre-functionalized substrates

• diborons can capture the in situ-generated carbon-centered radicals [28][29][30][31][32][33][34][35][36]. Among the aryl sources in organic synthesis, triarylbismuthines are shelf-stable and easy-to-handle reagents with appropriate reactivities in transition-metal-catalyzed reactions and radical reactions

Transition-metal-catalyst-free electroreductive alkene hydroarylation with aryl halides under visible-light irradiation

• Kosuke Yamamoto,
• Kazuhisa Arita,
• Masami Kuriyama and
• Osamu Onomura

Beilstein J. Org. Chem. 2024, 20, 1327–1333, doi:10.3762/bjoc.20.116

• versatile building blocks in organic syntheses. To achieve this transformation with high efficiency and predictable regioselectivity, numerous efforts have been made to develop transition-metal-catalyzed reactions based on a C–H activation strategy [1][2][3][4] or the reductive coupling of aryl halides with

HPW-Catalyzed environmentally benign approach to imidazo[1,2-a]pyridines

• Luan A. Martinho and
• Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2024, 20, 628–637, doi:10.3762/bjoc.20.55

• (insomnia). Some recent synthetic approaches to imidazo[1,2-a]pyridine scaffolds include synthetic pathways of transition metal-catalyzed reactions [14], cyclization [15], condensation [16], heteroannular [17], and photocatalytic reactions [18]. These approaches usually involve non-trivial reaction

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

• )–H Functionalization of pyridine rings in bipyridine systems The functionalization and synthesis of bipyridine derivatives is of great interest and importance in synthetic chemistry. These compounds are well-studied for their roles as chelating ligands in transition-metal-catalyzed reactions

Mechanochemical halogenation of unsymmetrically substituted azobenzenes

• Dajana Barišić,
• Mario Pajić,
• Ivan Halasz,
• Darko Babić and
• Manda Ćurić

Beilstein J. Org. Chem. 2022, 18, 680–687, doi:10.3762/bjoc.18.69

• ; N-halosuccinimide; palladium(II); Introduction Electrophilic aromatic substitution [1][2][3] and ligand-directed transition-metal-catalyzed reactions [4][5][6][7][8] are among the most widely used synthetic approaches for the preparation of halogenated arenes. They are important precursors in cross

Iridium-catalyzed hydroacylation reactions of C1-substituted oxabenzonorbornadienes with salicylaldehyde: an experimental and computational study

• Angel Ho,
• Austin Pounder,
• Krish Valluru,
• Leanne D. Chen and
• William Tam

Beilstein J. Org. Chem. 2022, 18, 251–261, doi:10.3762/bjoc.18.30

• attractive. Transition-metal-catalyzed reactions of strained bicyclic derivatives have been an intense area of research in the last 20 years (Scheme 1) [14][15][16][17]. Of particular interest is oxabenzonorbornadiene (OBD, 1), as it bears multiple points of reactivity that allow for diverse

Recent advances and perspectives in ruthenium-catalyzed cyanation reactions

• Thaipparambil Aneeja,
• Cheriya Mukkolakkal Abdulla Afsina,
• Padinjare Veetil Saranya and
• Gopinathan Anilkumar

Beilstein J. Org. Chem. 2022, 18, 37–52, doi:10.3762/bjoc.18.4

• demanded the need of an alternative method for the synthesis of nitriles. Nowadays transition-metal-catalyzed reactions have received tremendous interest. Various transition metals such as Fe [15], Co [16], Ni [17], Pd [18], Cu [19], Rh [20] etc. were well explored in cyanation owing to its cost-effective

Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

• Umesh P. Aher,
• Dhananjai Srivastava,
• Girij P. Singh and
• Jayashree B. S

Beilstein J. Org. Chem. 2021, 17, 2680–2715, doi:10.3762/bjoc.17.182

• introduction on important classical approaches and older yet creative methods to provide the reader with a historical context. For comparison, this will be followed by a discussion of more modern techniques, including chiral auxiliaries for neighboring group participation and transition metal-catalyzed

• reactions, along with recent new promoter-dependent advances. It is generally agreed that the stereochemical outcome of glycosylation can be affected by multiple factors [66][67][68][69], which include i) structure and conformation of the glycosyl substrates, ii) glycosylation reagents or promoters, iii

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

• ][27][28]. Various approaches starting from functionalized biaryls have hereby attracted considerable interest, since the precursors are readily available by established cross-coupling reactions. Beyond transition-metal-catalyzed reactions, acid-mediated cyclizations of biphenylcarboxylic acids and

1,2,3-Triazoles as leaving groups: S_NAr reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles

• Dace Cīrule,
• Irina Novosjolova,
• Ērika Bizdēna and
• Māris Turks

Beilstein J. Org. Chem. 2021, 17, 410–419, doi:10.3762/bjoc.17.37

• is introduced at the C6 position of the purine ring using SNAr reactions (Ia→II, Scheme 1). If purine contains identical leaving groups at C2 and C6 positions the reactivity order in its SNAr reactions is C6 > C2 [71][72]. Also transition metal catalyzed reactions can be used for C6 functionalization

Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups

• Xiaowei Li,
• Xiaolin Shi,
• Xiangqian Li and
• Dayong Shi

Beilstein J. Org. Chem. 2019, 15, 2213–2270, doi:10.3762/bjoc.15.218

• review covers mainly two types of transition-metal-catalyzed reactions: 1) cross-couplings with a fluorinated organometallic species or a halogenated fluorinated species and 2) the direct introduction of fluorinated moieties into nonfunctionalized substrates with a fluorinated reagent. We hope that this

Synthesis of benzo[d]imidazo[2,1-b]benzoselenoazoles: Cs₂CO₃-mediated cyclization of 1-(2-bromoaryl)benzimidazoles with selenium

• Mio Matsumura,
• Yuki Kitamura,
• Arisa Yamauchi,
• Yoshitaka Kanazawa,
• Yuki Murata,
• Tadashi Hyodo,
• Kentaro Yamaguchi and
• Shuji Yasuike

Beilstein J. Org. Chem. 2019, 15, 2029–2035, doi:10.3762/bjoc.15.199

• , reaction 3) [8]. However, to the best of our knowledge, the synthesis of imidazoselenoazoles has been limited to highly substituted derivatives and the basic physical properties of the parent skeleton have not been clarified. Transition metal-catalyzed reactions are one of the most popular methods to form

Synergistic approach to polycycles through Suzuki–Miyaura cross coupling and metathesis as key steps

• Sambasivarao Kotha,
• Milind Meshram and
• Chandravathi Chakkapalli

Beilstein J. Org. Chem. 2018, 14, 2468–2481, doi:10.3762/bjoc.14.223

• -Doctoral Fellow at the KU Leuven, Belgium under the EMINTE programme. During post-doctoral work his research work was related to organic synthesis under microwave reaction conditions. Presently, he is Research Associate with Prof. S. Kotha. His research interests include various transition-metal-catalyzed

• reactions and their applications in organic synthesis. Chandravathi Chakkapalli obtained her B.Sc. and M.Sc. in Chemistry from Andhra University, Andhra Pradesh, India. She completed her Ph.D. under the supervision of Dr. J. S. Yadav from IICT, Hyderabad in 2016. Her research interests are in the area of

Cobalt-catalyzed C–H cyanations: Insights into the reaction mechanism and the role of London dispersion

• Eric Detmar,
• Valentin Müller,
• Daniel Zell,
• Lutz Ackermann and
• Martin Breugst

Beilstein J. Org. Chem. 2018, 14, 1537–1545, doi:10.3762/bjoc.14.130

• ][10][11], London dispersion can also play a crucial role in different transition-metal-catalyzed reactions [12][13][14][15][16][17]. The C–H-rich di-1-adamantylphosphine oxide – a typical dispersion element – was experimentally found to be an excellent preligand for ruthenium- and palladium-catalyzed

• exclusively act as a sterically demanding ligand in transition-metal-catalyzed reactions. Conclusion We have analyzed the cobalt(III)-catalyzed C–H cyanation of differently substituted 2-phenylpyridines with N-cyano-N-aryl-p-toluenesulfonamide using density functional theory. On the basis of our computational

Three-component coupling of aryl iodides, allenes, and aldehydes catalyzed by a Co/Cr-hybrid catalyst

• Kimihiro Komeyama,
• Shunsuke Sakiyama,
• Kento Iwashita,
• Itaru Osaka and
• Ken Takaki

Beilstein J. Org. Chem. 2018, 14, 1413–1420, doi:10.3762/bjoc.14.118

• organometallics, involving a wide range of transition metal-catalyzed reactions. For example, transmetalation between an organonickel (or organocobalt) complex and chromium salt results in the formation of a highly nucleophilic organochromium species, which enables efficient addition to aldehydes to give

Bromide-assisted chemoselective Heck reaction of 3-bromoindazoles under high-speed ball-milling conditions: synthesis of axitinib

• Jingbo Yu,
• Zikun Hong,
• Xinjie Yang,
• Yu Jiang,
• Zhijiang Jiang and
• Weike Su

Beilstein J. Org. Chem. 2018, 14, 786–795, doi:10.3762/bjoc.14.66

• transition-metal-catalyzed reactions [1][2], which has shown itself as a powerful synthetic tool in both academic and industrial practice [3][4][5][6][7]. The transformation has been enrolled as key steps for numerous synthetic routes, including the recent President Green Chemistry Award winner route of

The reductive decyanation reaction: an overview and recent developments

• Jean-Marc R. Mattalia

Beilstein J. Org. Chem. 2017, 13, 267–284, doi:10.3762/bjoc.13.30

• on transition-metal-catalyzed reactions focuses on selected examples that show the wide scope of reduced substrates including alkyl cyanides, challenging substrates due to their propensity to undergo β-hydride elimination from alkylmetal intermediates. Nakazawa et al. reported the photoinduced C–CN

Unusual reactions of diazocarbonyl compounds with α,β-unsaturated δ-amino esters: Rh(II)-catalyzed Wolff rearrangement and oxidative cleavage of N–H-insertion products

• Valerij A. Nikolaev,
• Jury J. Medvedev,
• Olesia S. Galkina,
• Ksenia V. Azarova and
• Christoph Schneider

Beilstein J. Org. Chem. 2016, 12, 1904–1910, doi:10.3762/bjoc.12.180

• ; transition-metal-catalyzed reactions; Wolff rearrangement; Introduction Transition-metal-catalyzed reactions of diazocarbonyl compounds (DCC) with different organic substrates comprise a powerful tool of organic synthesis [1][2][3][4][5][6][7][8]. Of prime importance was found to be the ability of reactive

On the cause of low thermal stability of ethyl halodiazoacetates

• Magnus Mortén,
• Martin Hennum and
• Tore Bonge-Hansen

Beilstein J. Org. Chem. 2016, 12, 1590–1597, doi:10.3762/bjoc.12.155

• transition metal-catalyzed reactions [5]. A large number of diazo esters have been synthesized and an order has been arranged for α-substituents that increase the stability of the diazoesters [3]. Halogen substituents are completely absent from this list of α-substituents. Hence, the relative position of

Conjugate addition–enantioselective protonation reactions

• James P. Phelan and
• Jonathan A. Ellman

Beilstein J. Org. Chem. 2016, 12, 1203–1228, doi:10.3762/bjoc.12.116

• , protodemetalation liberates the product and regenerates 69. While the overall process provides the same product as a conjugate addition–enantioselective protonation sequence, mechanistically this, along with other transition metal-catalyzed reactions that invoke a conjugate addition–enantioselective protonation

Iodine-mediated synthesis of 3-acylbenzothiadiazine 1,1-dioxides

• Long-Yi Xi,
• Ruo-Yi Zhang,
• Lei Shi,
• Shan-Yong Chen and
• Xiao-Qi Yu

Beilstein J. Org. Chem. 2016, 12, 1072–1078, doi:10.3762/bjoc.12.101

• reaction conditions, causing the formation of byproducts. An alternative route to the benzothiadiazine 1,1-dioxide ring are transition metal-catalyzed reactions. Various benzothiadiazine 1,1-dioxides were successfully prepared using this approach [16][17][18][19]. However, the separation of transitional

Spiro-fused carbohydrate oxazoline ligands: Synthesis and application as enantio-discrimination agents in asymmetric allylic alkylation

• Jochen Kraft,
• Martin Golkowski and
• Thomas Ziegler

Beilstein J. Org. Chem. 2016, 12, 166–171, doi:10.3762/bjoc.12.18

• of tertiary carbon stereocenters, remains an ongoing challenge. Over the last decades though, transition metal-catalyzed reactions like the asymmetric allylic alkylation (Tsuji–Trost reaction) have evolved into one of the more powerful tools for synthesizing such tertiary stereocenters [7][8]. As a