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

• material. Concurrently, implementing a scale-up synthesis procedure to exploit the application potential of rotaxane-based polymers induces structural ambiguities, thereby presenting a significant trade-off between realizing inexpensive production and defined structures. To overcome this rotaxane-synthesis

Synthesis of 2-benzyl N-substituted anilines via imine condensation–isoaromatization of (E)-2-arylidene-3-cyclohexenones and primary amines

• Lu Li,
• Na Li,
• Xiao-Tian Mo,
• Ming-Wei Yuan,
• Lin Jiang and
• Ming-Long Yuan

Beilstein J. Org. Chem. 2024, 20, 1468–1475, doi:10.3762/bjoc.20.130

• further demonstrated. As depicted in Scheme 5, we first attempted scale-up synthesis of product 4aa. Pleasingly, when starting from 2a on a 6.0 mmol scale, the product 4aa was afforded in 74% yield. We also conducted the successive synthesis of 4aa in a manner of one-pot procedure. On the condition of

Copper-catalyzed multicomponent reaction of β-trifluoromethyl β-diazo esters enabling the synthesis of β-trifluoromethyl N,N-diacyl-β-amino esters

• Youlong Du,
• Haibo Mei,
• Ata Makarem,
• Ramin Javahershenas,
• Vadim A. Soloshonok and
• Jianlin Han

Beilstein J. Org. Chem. 2024, 20, 212–219, doi:10.3762/bjoc.20.21

• . Control experiments. Proposed reaction mechanism. Scale-up synthesis. Optimization of reaction conditions.a Supporting Information Supporting Information File 8: Experimental details and spectral data. Funding We gratefully acknowledge the financial support from the National Natural Science Foundation

When metal-catalyzed C–H functionalization meets visible-light photocatalysis

• Lucas Guillemard and
• Joanna Wencel-Delord

Beilstein J. Org. Chem. 2020, 16, 1754–1804, doi:10.3762/bjoc.16.147

• , isolated in moderate to good yields. A possible gram scale-up synthesis was also accomplished. Within the mechanistic cycle, after initial vinylic C–H bond activation and insertion of CO into the C–Pd bond, the acylpalladium intermediate is converted into its conjugated analog under DABCO assistance

An efficient and concise access to 2-amino-4H-benzothiopyran-4-one derivatives

• Peng Li,
• Yongqi Wu,
• Tingting Zhang,
• Chen Ma,
• Ziyun Lin,
• Gang Li and
• Haihong Huang

Beilstein J. Org. Chem. 2019, 15, 703–709, doi:10.3762/bjoc.15.65

• and the substrate scope in terms of electronic properties of the substituents of the benzothiopyranone is broad. The ten grams scale-up synthesis of the representative compounds 4a and 4d was implemented to show the practical application of this reaction, which afforded the corresponding compounds in

• good yields and excellent chemical purity without requiring column chromatographical purification. Keywords: 2-amino-4H-benzothiopyran-4-ones; addition–elimination; scale-up synthesis; sulfinyl group; Introduction Benzothiopyranones are a class of molecules displaying biological activities in part

An efficient and facile access to highly functionalized pyrrole derivatives

• Meng Gao,
• Wenting Zhao,
• Hongyi Zhao,
• Ziyun Lin,
• Dongfeng Zhang and
• Haihong Huang

Beilstein J. Org. Chem. 2018, 14, 884–890, doi:10.3762/bjoc.14.75

• another simple dipolarophile was also examined; the target product 12k was prepared smoothly in high yield (74%). This concise and efficient protocol displays the potentiality for scale-up synthesis of pyrrolo[3,4-c]pyrrole-1,3-diones. Having the pyrrolo[3,4-c]pyrrole-1,3-diones with diversified

Extrusion – back to the future: Using an established technique to reform automated chemical synthesis

• Deborah E. Crawford

Beilstein J. Org. Chem. 2017, 13, 65–75, doi:10.3762/bjoc.13.9

• avoided. In summary, extrusion is a technique that has great potential for use in organic synthesis. It has already been demonstrated as a method to scale up synthesis carried out by ball milling, therefore there is very little preventing its use for the organic reactions that have been reported to be

Flow carbonylation of sterically hindered ortho-substituted iodoarenes

• Carl J. Mallia,
• Gary C. Walter and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2016, 12, 1503–1511, doi:10.3762/bjoc.12.147

• continuous flow hydroxy-carbonylation method. Flow carbonylation of 2-iodonaphtalene. Scale up synthesis of 2-chloro-4-fluorobenzoic acid (20). Optimisation for the carbonylation of ortho-substituted substrates in flow. Supporting Information Supporting Information File 427: Experimental part. Supporting

Catalytic asymmetric formal synthesis of beraprost

• Yusuke Kobayashi,
• Ryuta Kuramoto and
• Yoshiji Takemoto

Beilstein J. Org. Chem. 2015, 11, 2654–2660, doi:10.3762/bjoc.11.285

• improved to 85% ee while maintaining the high reactivity. Employing catalyst E we further investigated the reaction conditions and found that a scale-up synthesis can be performed using only 1 mol % of E with no loss of enantioselectivity, although gentle heating was required to ensure a high chemical

• exchange and subsequent addition to methyl 4-oxobutanoate was found to be the best method to introduce the C4 subunit with reproducibility in the case of scale-up synthesis. Deprotection of the resultant ester 23 followed by reduction of the benzylic OH group finally afforded the key intermediate 2

Efficient synthetic protocols for the preparation of common N-heterocyclic carbene precursors

• Morgan Hans,
• Jan Lorkowski,
• Albert Demonceau and
• Lionel Delaude

Beilstein J. Org. Chem. 2015, 11, 2318–2325, doi:10.3762/bjoc.11.252

• solvent and hinders scale up. Synthesis of 1,3-bis(2,6-diisopropylphenyl)imidazolinium chloride In most cases, experimental procedures leading to 1,3-dimesitylimidazolinium salts could be successfully extended to their 1,3-bis(2,6-diisopropylphenyl) counterparts without any adaptation. Thus, the three

Dicarboxylic esters: Useful tools for the biocatalyzed synthesis of hybrid compounds and polymers

• Ivan Bassanini,
• Karl Hult and
• Sergio Riva

Beilstein J. Org. Chem. 2015, 11, 1583–1595, doi:10.3762/bjoc.11.174

• traditional polymerization methods [52]. Binns et al. summarized the attempts to scale up synthesis of polyesters by enzyme catalyzed polycondensation of adipic acid and hexane-1,6-diol in a very well-worth reading article [53]. They discussed the very slow progress in achieving high molecular weight polymers

Continuous flow photocyclization of stilbenes – scalable synthesis of functionalized phenanthrenes and helicenes

• Quentin Lefebvre,
• Marc Jentsch and
• Magnus Rueping

Beilstein J. Org. Chem. 2013, 9, 1883–1890, doi:10.3762/bjoc.9.221

• . Photo-flow synthesis of [5]- and [6]helicenes. aFor experimental details see Supporting Information File 1. bReaction conditions: 1.1 equiv iodine, 20 equiv THF, UV-light, 2 h retention time. Scale up synthesis of the [5]helicene derivative 2o. Proof of principle and screening of reaction conditions

A scalable synthesis of the (S)-4-(tert-butyl)-2-(pyridin-2-yl)-4,5-dihydrooxazole ((S)-t-BuPyOx) ligand

• Hideki Shimizu,
• Jeffrey C. Holder and
• Brian M. Stoltz

Beilstein J. Org. Chem. 2013, 9, 1637–1642, doi:10.3762/bjoc.9.187

• synthesis and revised plan. Scale-up synthesis of (S)-t-BuPyOx. Amidation reactions of picolinic acid. Cyclization screen. Supporting Information Materials and methods, auxiliary experimental details, and relevant NMR spectra are provided. Supporting Information File 382: Experimental details

Efficient syntheses of 25,26-dihydrodictyostatin and 25,26-dihydro-6-epi-dictyostatin, two potent new microtubule-stabilizing agents

• María Jiménez,
• Wei Zhu,
• Andreas Vogt,
• Billy W. Day and
• Dennis P. Curran

Beilstein J. Org. Chem. 2011, 7, 1372–1378, doi:10.3762/bjoc.7.161

• minor isomer along with about 75% of the target isomer. The subsequent testing data identify 25,26-dihydrodictyostatin and 25,26-dihydro-6-epi-dictyostatin as candidates for scale-up synthesis and further preclinical development. Structures of dictyostatin and selected analogs varying at C6, C16, and

Triple-channel microreactor for biphasic gas–liquid reactions: Photosensitized oxygenations

• Ram Awatar Maurya,
• Chan Pil Park and
• Dong-Pyo Kim

Beilstein J. Org. Chem. 2011, 7, 1158–1163, doi:10.3762/bjoc.7.134

• (Table 2). To compare the productivity for scale-up synthesis, the space–time yield of the triple-channel microreactor and that of the round bottom flask was calculated at various times during the course of the reaction. The space–time yield data reveals that triple-channel microreactors are quite