Rhodium-catalyzed reductive carbonylation of aryl iodides to arylaldehydes with syngas

• Zhenghui Liu,
• Peng Wang,
• Zhenzhong Yan,
• Suqing Chen,
• Dongkun Yu,
• Xinhui Zhao and
• Tiancheng Mu

Beilstein J. Org. Chem. 2020, 16, 645–656, doi:10.3762/bjoc.16.61

• , the appropriate amount of Et3N was set at 1.2 mmol. Effect of solvents Solvents act as the reaction media and strongly influence the catalytic reactions [52][53]. We screened nine representative solvents in the catalytic reaction and the results are summarized in Figure 1c. Apparently, protic solvents

Aerobic synthesis of N-sulfonylamidines mediated by N-heterocyclic carbene copper(I) catalysts

• Faïma Lazreg,
• Marie Vasseur,
• Alexandra M. Z. Slawin and
• Catherine S. J. Cazin

Beilstein J. Org. Chem. 2020, 16, 482–491, doi:10.3762/bjoc.16.43

• reaction between 6 and 8. Synthesis of copper-acetylide intermediate A via [Cu(Cl)(Triaz)]. Catalytic reaction involving copper-acetylide complex A. Catalyst and solvent optimisation.a,b Supporting Information Supporting Information File 139: Experimental and characterisation data. Supporting Information

Synthesis of six-membered silacycles by borane-catalyzed double sila-Friedel–Crafts reaction

• Yafang Dong,
• Masahiko Sakai,
• Kazuto Fuji,
• Kohei Sekine and
• Yoichiro Kuninobu

Beilstein J. Org. Chem. 2020, 16, 409–414, doi:10.3762/bjoc.16.39

• in terms of the functional group tolerance and versatility of these previously reported synthetic methods due to the use of a stoichiometric amount of the organolithium reagents. In addition, despite these contributions, catalytic reaction systems have not been developed as much [26][27]. The sila

• benzosiloles [39]. We have also contributed to the synthesis of silafluorenes from biphenyls and dihydrosilanes using a borane-catalyzed double sila-Friedel–Crafts reaction [40][41]. Subsequently, we envisaged that the catalytic reaction between diaryl ethers and dihydrosilanes may be a useful protocol to

Synthesis and herbicidal activities of aryloxyacetic acid derivatives as HPPD inhibitors

• Man-Man Wang,
• Hao Huang,
• Lei Shu,
• Jian-Min Liu,
• Jian-Qiu Zhang,
• Yi-Le Yan and
• Da-Yong Zhang

Beilstein J. Org. Chem. 2020, 16, 233–247, doi:10.3762/bjoc.16.25

• dark blue sphere. The commonly recognized HPPD catalytic reaction mechanism. Synthetic route of the title compounds I. Reagents and conditions: (a) methyl chloroacetate, K2CO3, CH3CN, 65 °C; (b) K2CO3, H2O, 65 °C; (c) aqueous HCl solution (10%), rt; (d) substituted 1,3-cyclohexanediones, EDCI, DMAP

Combining the Ugi-azide multicomponent reaction and rhodium(III)-catalyzed annulation for the synthesis of tetrazole-isoquinolone/pyridone hybrids

• Gerardo M. Ojeda,
• Prabhat Ranjan,
• Pavel Fedoseev,
• Lisandra Amable,
• Upendra K. Sharma,
• Daniel G. Rivera and
• Erik V. Van der Eycken

Beilstein J. Org. Chem. 2019, 15, 2447–2457, doi:10.3762/bjoc.15.237

• rhodium catalyst to promote C(sp2)–H activation in the presence of a suitable directing group. The Ugi-azide reaction provides broad molecular diversity and enables the introduction of the tetrazole moiety, which may further assist the catalytic reaction by coordinating the metal center. The scope of the

• tetrazole ring takes part in the catalytic reaction mechanism by chelating Rh(III) upon activation of the amide ortho-position. This work illustrates the synthetic potential of combining isocyanide-based multicomponent reactions with metal-catalyzed transformations to generate structural diversity and

Naphthalene diimides with improved solubility for visible light photoredox catalysis

• Barbara Reiß and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2019, 15, 2043–2051, doi:10.3762/bjoc.15.201

• catalytic activity was representatively tested by the MacMillan benchmark reaction [53]. For this type of photoredox catalytic reaction, solubility of cNDIs in DMF is a crucial prerequisite. Results and Discussion Synthesis of cNDIs 2–6 and their solubility The commercially available precursor for all NDIs

• %. The emission of this LED overlays well with the absorbance of cNDI 6 (Figure 2). As expected, the photoredox catalytic reaction with cNDI 6 is much “cleaner” than with NDI 1 and the substrate conversion differs only slightly from the product yield. Taken together, cNDI 6 is a suitable visible light

• evaluated for the MacMillan benchmark reaction. This photoredox catalytic reaction in the presence of cNDI 6 was much “cleaner” than with NDI 1 since the conversions differed only slightly from the product yields. Irradiations were performed with LEDs in the visible light range between 520 nm and 640 nm

Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage

• Gagandeep Kour Reen,
• Ashok Kumar and
• Pratibha Sharma

Beilstein J. Org. Chem. 2019, 15, 1612–1704, doi:10.3762/bjoc.15.165

Synthesis of non-racemic 4-nitro-2-sulfonylbutan-1-ones via Ni(II)-catalyzed asymmetric Michael reaction of β-ketosulfones

• Alexander N. Reznikov,
• Anastasiya E. Sibiryakova,
• Marat R. Baimuratov,
• Eugene V. Golovin,
• Victor B. Rybakov and
• Yuri N. Klimochkin

Beilstein J. Org. Chem. 2019, 15, 1289–1297, doi:10.3762/bjoc.15.127

• , and, on the other hand, the ratio of diastereomers in the presence of the same catalyst strongly depends on the solvent used. This suggests that the dr is determined by the rates ratio of the catalytic reaction (which can occur with high or low diastereoselectivity) and the epimerization of products

Reusable and highly enantioselective water-soluble Ru(II)-Amm-Pheox catalyst for intramolecular cyclopropanation of diazo compounds

• Hamada S. A. Mandour,
• Yoko Nakagawa,
• Masaya Tone,
• Hayato Inoue,
• Nansalmaa Otog,
• Ikuhide Fujisawa,
• Soda Chanthamath and
• Seiji Iwasa

Beilstein J. Org. Chem. 2019, 15, 357–363, doi:10.3762/bjoc.15.31

• cyclization of trans-allylic diazo Weinreb amide 1f catalyzed by Ru(II)-Amm-Pheox (cat. 2) was examined in various solvents, as shown in Table S1 (Supporting Information File 1). Notably, the catalytic reaction proceeded in a variety of solvents, including aromatic, aliphatic, polar, non-polar, and

Tandem copper and photoredox catalysis in photocatalytic alkene difunctionalization reactions

• Nicholas L. Reed,
• Madeline I. Herman,
• Vladimir P. Miltchev and
• Tehshik P. Yoon

Beilstein J. Org. Chem. 2019, 15, 351–356, doi:10.3762/bjoc.15.30

• unless otherwise noted. a3:1 dr. b10:1 dr. cReaction conducted using MesAcrMe+ (6) as photocatalyst. Optimization of dual-catalytic reaction conditionsa. Supporting Information Supporting Information File 26: Full experimental details for all reactions. Acknowledgements This work was funded by the NIH

Recent advances in hypervalent iodine(III)-catalyzed functionalization of alkenes

• Xiang Li,
• Pinhong Chen and
• Guosheng Liu

Beilstein J. Org. Chem. 2018, 14, 1813–1825, doi:10.3762/bjoc.14.154

• synthesized and applied [72]. The regioselective methoxylation of diphenyl alkene with chiral hypervalent iodine 58 afforded a mixture of 60 and 61 in moderated yield and good enantioselectivity. However, the catalytic reaction afforded the opposite regioselectivity to give rearrangement product 60 in

Synthesis of spirocyclic scaffolds using hypervalent iodine reagents

• Fateh V. Singh,
• Priyanka B. Kole,
• Saeesh R. Mangaonkar and
• Samata E. Shetgaonkar

Beilstein J. Org. Chem. 2018, 14, 1778–1805, doi:10.3762/bjoc.14.152

• TsOH·H2O as additive and 1.8 equivalents of mCPBA as oxidant. The catalytic reaction was carried out in nitromethane at 50 °C for 23 h and spirolactone 36 was isolated in 74% yield (Scheme 9). It was noted that 20 mol % of additive was essential to initiate the reaction efficiently. The reaction was quite

Phosphodiester models for cleavage of nucleic acids

• Satu Mikkola,
• Tuomas Lönnberg and
• Harri Lönnberg

Beilstein J. Org. Chem. 2018, 14, 803–837, doi:10.3762/bjoc.14.68

Progress in copper-catalyzed trifluoromethylation

• Guan-bao Li,
• Chao Zhang,
• Chun Song and
• Yu-dao Ma

Beilstein J. Org. Chem. 2018, 14, 155–181, doi:10.3762/bjoc.14.11

• . Although this catalytic reaction worked efficiently, the trifluoromethyl source TESCF3 was expensive and relatively inaccessible, which made this process less economic, especially for large-scale synthesis. In 2014, Novák, Kotschy and co-workers [13] developed a new procedure with the relatively cheap and

Rh(II)-mediated domino [4 + 1]-annulation of α-cyanothioacetamides using diazoesters: A new entry for the synthesis of multisubstituted thiophenes

• Jury J. Medvedev,
• Ilya V. Efimov,
• Yuri M. Shafran,
• Vitaliy V. Suslonov,
• Vasiliy A. Bakulev and
• Valerij A. Nikolaev

Beilstein J. Org. Chem. 2017, 13, 2569–2576, doi:10.3762/bjoc.13.253

• , entry 6). Thus the experiments with diazomalonate 2a and thioacetamide 1a demonstrated that the most appropriate conditions for the catalytic reaction of a diazo carbonyl compound with thioamides, were the employment of an 1.2-fold excess of diazoester 2, Rh2(OAc)4 or Rh2(OPiv)4 as the catalysts, and

• the same molecule. The main objective of our current research was to study Rh(II)-catalyzed reactions of diazocarbonyl compounds with α-cyanothioacetamides, bearing both thioamide and cyano groups in their structure. Based on the known literature findings [36][37][38] one might expect that a catalytic

• reaction of diazocarbonyl compounds with α-cyanothioacetamides would first of all affect the electron-rich sulfur atom of the C=S group, leading to the generation of intermediate thiocarbonyl ylides, which would further react intramolecularly with the cyano group to produce a heterocyclic structure. One

Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinoline and 1,2,3-triazole

• Martina Tireli,
• Silvija Maračić,
• Stipe Lukin,
• Marina Juribašić Kulcsár,
• Dijana Žilić,
• Mario Cetina,
• Ivan Halasz,
• Silvana Raić-Malić and
• Krunoslav Užarević

Beilstein J. Org. Chem. 2017, 13, 2352–2363, doi:10.3762/bjoc.13.232

• transformation of reactants to products. Thus, we propose that the catalytic reaction for the method 2c is most likely occurring on the surface of brass milling balls, with minute diffusion of the copper ions to the reaction mixture. During the milling reactions, copper(0) and copper(I) catalysts do not oxidize

Is the tungsten(IV) complex (NEt₄)₂[WO(mnt)₂] a functional analogue of acetylene hydratase?

• Matthias Schreyer and
• Lukas Hintermann

Beilstein J. Org. Chem. 2017, 13, 2332–2339, doi:10.3762/bjoc.13.230

• (ethanal; 3) by redox-neutral addition of water (Scheme 1a) [2][3][4][5][6]. Even based on X-ray structural data of the enzyme [4], the catalytic reaction mechanism was not immediately obvious [4][7]. Several mechanisms have so far been considered and investigated in silico [8][9][10][11][12]. The most

Mechanochemical synthesis of thioureas, ureas and guanidines

• Vjekoslav Štrukil

Beilstein J. Org. Chem. 2017, 13, 1828–1849, doi:10.3762/bjoc.13.178

• time to 4 hours and increasing the catalyst loading to 10–20 mol %. In general, there was no reactivity without CuCl, in solution or in the presence of a base instead of CuCl, implying that CuCl activated the carbodiimide component during this catalytic reaction. Tan and Friščić further developed this

NHC-catalyzed cleavage of vicinal diketones and triketones followed by insertion of enones and ynones

• Ken Takaki,
• Makoto Hino,
• Akira Ohno,
• Kimihiro Komeyama,
• Hiroto Yoshida and
• Hiroshi Fukuoka

Beilstein J. Org. Chem. 2017, 13, 1816–1822, doi:10.3762/bjoc.13.176

• study on the multicomponent reaction of thiazolium carbenes, benzils and water to yield 1,4-thiazin-3-ones [22]. Although the initial process producing the salt 12 was similar, the total mode of the two reactions was quite different, that is, stoichiometric vs catalytic reaction with respect to the

Ni nanoparticles on RGO as reusable heterogeneous catalyst: effect of Ni particle size and intermediate composite structures in C–S cross-coupling reaction

• Debasish Sengupta,
• Koushik Bhowmik,
• Goutam De and
• Basudeb Basu

Beilstein J. Org. Chem. 2017, 13, 1796–1806, doi:10.3762/bjoc.13.174

• of NPs or further oxidation of Ni NPs in the absence of the electron-rich RGO surface. Thus, the average size of Ni NPs supported with electron-rich RGO surface seems to be important to obtain maximum catalytic efficiency in the C–S coupling reaction. The catalytic reaction was found to be scalable

An effective Pd nanocatalyst in aqueous media: stilbene synthesis by Mizoroki–Heck coupling reaction under microwave irradiation

• Carolina S. García,
• Paula M. Uberman and
• Sandra E. Martín

Beilstein J. Org. Chem. 2017, 13, 1717–1727, doi:10.3762/bjoc.13.166

• modified, and probably this structure is responsible for the activity since it leaves enough surface available to perform the catalytic reaction. Conclusion In summary, the PVP-Pd NPs exhibit an outstanding catalytic activity in the Mizoroki–Heck reaction under environmentally friendly reaction conditions

Synthesis of alkynyl-substituted camphor derivatives and their use in the preparation of paclitaxel-related compounds

• M. Fernanda N. N. Carvalho,
• Rudolf Herrmann and
• Gabriele Wagner

Beilstein J. Org. Chem. 2017, 13, 1230–1238, doi:10.3762/bjoc.13.122

• substituents at the triple bonds have a decisive influence on the outcome of the catalytic reaction. This was also confirmed by the reaction of 4e (R = benzyl): in addition to the expected product 7 in analogy to that of 4b, there was also a considerable amount of a reduced species 10 lacking sulphur reduction

Sugar-based micro/mesoporous hypercross-linked polymers with in situ embedded silver nanoparticles for catalytic reduction

• Qing Yin,
• Qi Chen,
• Li-Can Lu and
• Bao-Hang Han

Beilstein J. Org. Chem. 2017, 13, 1212–1221, doi:10.3762/bjoc.13.120

• an excess amount of NaBH4 as the reducing reagent [45]. In our study, the process of the catalytic reaction was readily followed as the color of the solution turned from yellow to colorless. Both the reactants and products are easily monitored by UV–vis spectroscopy without any formation of

Towards open-ended evolution in self-replicating molecular systems

• Herman Duim and
• Sijbren Otto

Beilstein J. Org. Chem. 2017, 13, 1189–1203, doi:10.3762/bjoc.13.118

• ligase E’ can then in turn promote the formation of E, as depicted in Figure 8a. But this cross-catalytic reaction typically occurs at a very slow rate. In order to enhance this rate, enzymatic in vitro evolution of the RNA molecules was performed in order to obtain a set of fast replicating species. It

Automating multistep flow synthesis: approach and challenges in integrating chemistry, machines and logic

• Chinmay A. Shukla and
• Amol A. Kulkarni

Beilstein J. Org. Chem. 2017, 13, 960–987, doi:10.3762/bjoc.13.97