Simple synthesis of multi-halogenated alkenes from 2-bromo-2-chloro-1,1,1-trifluoroethane (halothane)

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

Beilstein J. Org. Chem. 2022, 18, 1567–1574, doi:10.3762/bjoc.18.167

• ) has been used as a fluorine-containing building block for the construction of trifluoromethyl and difluoromethylene motifs [1][2]. Such structures have been found in several multifunctional materials and biologically important molecules (Figure 1) [3][4][5][6][7]. The halothane structure contains two

Characterization of a new fusicoccane-type diterpene synthase and an associated P450 enzyme

• Jia-Hua Huang,
• Jian-Ming Lv,
• Liang-Yan Xiao,
• Qian Xu,
• Fu-Long Lin,
• Gao-Qian Wang,
• Guo-Dong Chen,
• Sheng-Ying Qin,
• Dan Hu and
• Hao Gao

Beilstein J. Org. Chem. 2022, 18, 1396–1402, doi:10.3762/bjoc.18.144

• Talaromyces wortmannii ATCC 26942, in which TadA is identified to be a new FC-type DTS responsible for the formation of talaro-7,13-diene, and the associated P450 enzyme TadB is characterized to be a multifunctional enzyme, converting talaro-7,13-diene to highly oxygenated talaro-6,13-dien-5,8-dione. Results

• Information File 1, Figures S33 and S34). The highly oxidized properties of talaro-6,13-dien-5,8-dione (4) indicate that TadB is a multifunctional P450 enzyme (Scheme 1A). Since no other intermediates were obtained, we could not determine the exact order of TadB-mediated oxidation, or exclude the possibility

Cytochrome P450 monooxygenase-mediated tailoring of triterpenoids and steroids in plants

• Karan Malhotra and
• Jakob Franke

Beilstein J. Org. Chem. 2022, 18, 1289–1310, doi:10.3762/bjoc.18.135

• selected recent examples of multifunctional CYPs that catalyse particularly remarkable modifications of triterpenoids. We therefore hope to provide an up-to-date overview over these key enzymes in plant triterpenoid and steroid metabolism since the last comparable endeavour from Ghosh in 2017 [7]. In

• ) function as sterol 14α-demethylases in green plants [24][25][98]. These enzymes catalyse oxidation of the C14α methyl group to trigger elimination of formic acid [24][25]. The sister subfamily CYP51H, on the other hand, is only found in monocots. AsCYP51H10 from Avena sativa (oat) is a multifunctional CYP

• scaffold in plants from the Cucurbitaceae family (Figure 3B). CYP87D18 (CYP85 clan) was identified as a multifunctional C11 oxidase involved in the biosynthetic pathway of mogrosides. Mogrosides, isolated from ripe fruits of Siraitia grosvenorii (Cucurbitaceae) are glycosylated triterpenoid saponins with

From amines to (form)amides: a simple and successful mechanochemical approach

• Federico Casti,
• Rita Mocci and
• Andrea Porcheddu

Beilstein J. Org. Chem. 2022, 18, 1210–1216, doi:10.3762/bjoc.18.126

• assistance with the generation of the 1H, 13C NMR, and GC–MS spectroscopic data. Funding This research was funded by MIUR Italy, PRIN 2017 project (grant number: 2017B7MMJ5_001) “MultIFunctional poLymer cOmposites based on groWn matERials (MIFLOWER) and Fondazione di Sardegna (FdS, F72F20000230007).

Reductive opening of a cyclopropane ring in the Ni(II) coordination environment: a route to functionalized dehydroalanine and cysteine derivatives

• Oleg A. Levitskiy,
• Olga I. Aglamazova,
• Yuri K. Grishin and
• Tatiana V. Magdesieva

Beilstein J. Org. Chem. 2022, 18, 1166–1176, doi:10.3762/bjoc.18.121

• construction of complex multifunctional molecules [3][4][5][6][7][8]. Recently, we elaborated a versatile electrochemical approach for the stereoselective functionalization of a side chain of amino acids involved in the Ni(II) chiral coordination environment [9][10][11][12][13][14][15]. A combination of redox

• due to the bioactivity of such compounds [56][57]; thus, elaboration of new synthetic protocols to these multifunctional molecules is a topical problem. Complex 4 was subjected to reductive ring opening at a potential of −1.5 V (Ag/AgCl, KCl(sat.)) in the presence of an equimolar amount of azobenzene

A trustworthy mechanochemical route to isocyanides

• Francesco Basoccu,
• Federico Cuccu,
• Federico Casti,
• Rita Mocci,
• Claudia Fattuoni and
• Andrea Porcheddu

Beilstein J. Org. Chem. 2022, 18, 732–737, doi:10.3762/bjoc.18.73

• Ricerca d'Ateneo) core facility of the University of Cagliari and Dr. Sandrina Lampis for assistance with the generation of the 1H and 13C NMR spectroscopic data. Funding This research was funded by MIUR Italy, PRIN 2017 project (grant number: 2017B7MMJ5_001) “MultIFunctional poLymer cOmposites based on

Direct C–H amination reactions of arenes with N-hydroxyphthalimides catalyzed by cuprous bromide

• Dongming Zhang,
• Bin Lv,
• Pan Gao,
• Xiaodong Jia and
• Yu Yuan

Beilstein J. Org. Chem. 2022, 18, 647–652, doi:10.3762/bjoc.18.65

• constructing C–N bonds are in high demand in organic synthesis since nitrogen-containing organic compounds are widely used in biologically active substances [1], multifunctional materials [2][3], and metal ligands [4][5]. Among them, the synthesis of aromatic amines has been important to researchers in recent

Bioinspired tetraamino-bisthiourea chiral macrocycles in catalyzing decarboxylative Mannich reactions

• Hao Guo,
• Yu-Fei Ao,
• De-Xian Wang and
• Qi-Qiang Wang

Beilstein J. Org. Chem. 2022, 18, 486–496, doi:10.3762/bjoc.18.51

• the above control experiments, the rigid macrocyclic framework is crucial in organizing the multiple functional sites for cooperative binding and activation. Conclusion In conclusion, a series of multifunctional tetraamino-bisthiourea chiral macrocycles were efficiently synthesized. By using a modular

• , we believe this type of biomimetic chiral macrocycles will find more applications as catalysts in other reactions. Design of PKS-inspired multifunctional amino-thiourea macrocycle catalysts. Proposed catalytic mechanism. Synthesis of tetraamino-bisthiourea chiral macrocycles M1–M12. The synthesis of

New advances in asymmetric organocatalysis

• Radovan Šebesta

Beilstein J. Org. Chem. 2022, 18, 240–242, doi:10.3762/bjoc.18.28

• combination of activation modes in bifunctional or multifunctional catalysis. Important is also a “green” aspect of organocatalysis as well as its fruitful overlap with many sustainability ideas [15]. In 2012, there has been a thematic issue of the Beilstein Journal of Organic Chemistry devoted to asymmetric

Asymmetric organocatalytic Michael addition of cyclopentane-1,2-dione to alkylidene oxindole

• Estelle Silm,
• Ivar Järving and
• Tõnis Kanger

Beilstein J. Org. Chem. 2022, 18, 167–173, doi:10.3762/bjoc.18.18

• presence of a multifunctional squaramide catalyst. Michael adducts were obtained in high enantioselectivities and in moderate diastereoselectivities. Keywords: cyclopentane-1,2-dione; enantioselective catalysis; Michael addition; organocatalysis; squaramide; Introduction Diketones are generally very

• malonates [25]. Herein, we report the results of an asymmetric organocatalytic Michael addition of CPD to alkylidene oxindoles. Results and Discussion Chiral multifunctional thioureas [26][27] and squaramides [28] are extensively used as catalysts in asymmetric Michael additions. We believed that a

Recent advances in organocatalytic asymmetric aza-Michael reactions of amines and amides

• Pratibha Sharma,
• Raakhi Gupta and
• Raj K. Bansal

Beilstein J. Org. Chem. 2021, 17, 2585–2610, doi:10.3762/bjoc.17.173

• yields ranged 57–89% with ee 70–97% [52]. A similar chiral multifunctional thiourea/boronic acid was used as an organocatalyst by Michigami et al. for the enantioselective synthesis of N-hydroxyaspartic acid derivatives 76 with perfect regioselectivity and high enantioselectivity (Table 17) [53

• -quinone methides. Asymmetric intermolecular aza-Michael addition of (E)-3-substituted-2-enoic acid. Asymmetric aza-Michael addition reaction for the synthesis of N-hydroxyaspartic acid derivatives catalyzed by chiral multifunctional thiourea/boronic acid. Intramolecular aza-Michael addition catalyzed by

Cryogels: recent applications in 3D-bioprinting, injectable cryogels, drug delivery, and wound healing

• Luke O. Jones,
• Leah Williams,
• Tasmin Boam,
• Martin Kalmet,
• Chidubem Oguike and
• Fiona L. Hatton

Beilstein J. Org. Chem. 2021, 17, 2553–2569, doi:10.3762/bjoc.17.171

• , gelatin sponge, gauze, and QCSG/CNT0 [116]. Cryogels comprising the natural biopolymers silk fibroin and chitosan, with tannic acid and ferric ions (Fe3+) incorporated have been reported as multifunctional devices for wound healing providing hemostasis, exudate absorbance, antibacterial effects, and

Copper-catalyzed monoselective C–H amination of ferrocenes with alkylamines

• Zhen-Sheng Jia,
• Qiang Yue,
• Ya Li,
• Xue-Tao Xu,
• Kun Zhang and
• Bing-Feng Shi

Beilstein J. Org. Chem. 2021, 17, 2488–2495, doi:10.3762/bjoc.17.165

• development of efficient methods to access multifunctional ferrocenes has attracted tremendous attention. Conventionally, functionalized ferrocenes were derived via electrophilic aromatic substitution mediated by strong Lewis acids or direct metalation using strong bases, such as alkyllithium reagents [3][9

Exfoliated black phosphorous-mediated CuAAC chemistry for organic and macromolecular synthesis under white LED and near-IR irradiation

• Azra Kocaarslan,
• Zafer Eroglu,
• Önder Metin and
• Yusuf Yagci

Beilstein J. Org. Chem. 2021, 17, 2477–2487, doi:10.3762/bjoc.17.164

• -hydroxypropan-1-ol) ether (Az-3), and 1-(prop-2-yn-1-yloxy)-2,2-bis((prop-2-yn-1-yloxy)methyl)butane (Alk-5) as multifunctional click components were irradiated in the presence of BPNs and CuII ligand under NIR light. The gelation was completed after 24 h (Scheme 3). The photocuring process was also followed by

• multifunctional monomers, Az-3 and Alk-5. Photoinduced CuAAC between benzyl azide and various alkynesa using exfoliated BPNsb in DMSO-d6 = 1 g/L. Supporting Information Supporting Information File 308: Characterisation data: 1H NMR spectra of Alk-1, Alk-2 and Alk-3, TEM, HAADF-STEM and associated EDS elemental

Constrained thermoresponsive polymers – new insights into fundamentals and applications

• Patricia Flemming,
• Alexander S. Münch,
• Andreas Fery and
• Petra Uhlmann

Beilstein J. Org. Chem. 2021, 17, 2123–2163, doi:10.3762/bjoc.17.138

• , have been intensively studied in solution. For the application of such polymers in novel sensors, drug delivery systems or as multifunctional coatings, they typically have to be transferred into specific arrangements, such as micelles, polymer films or grafted nanoparticles. However, it turns out that

Towards new NIR dyes for free radical photopolymerization processes

• Haifaa Mokbel,
• Guillaume Noirbent,
• Didier Gigmes,
• Frédéric Dumur and
• Jacques Lalevée

Beilstein J. Org. Chem. 2021, 17, 2067–2076, doi:10.3762/bjoc.17.133

• acrylate function conversion (FC) measured were higher than 80%. Such a high reactive function conversion is quite high for multifunctional monomers (with PETIA being a trifunctional acrylic monomer). Moreover, for the majority of the proposed systems, the photopolymerization starts as soon as the light is

Volatile emission and biosynthesis in endophytic fungi colonizing black poplar leaves

• Christin Walther,
• Pamela Baumann,
• Katrin Luck,
• Beate Rothe,
• Peter H. W. Biedermann,
• Jonathan Gershenzon,
• Tobias G. Köllner and
• Sybille B. Unsicker

Beilstein J. Org. Chem. 2021, 17, 1698–1711, doi:10.3762/bjoc.17.118

• ). CxTPS1 was a multifunctional enzyme in vitro and produced the monoterpenes myrcene (9) and (E)-β-ocimene (10) from GPP, the sesquiterpene (E,E)-α-farnesene (12) from FPP, and the diterpenes (E,E)-β-springene (13) and (E,E,E)-α-springene (14) from GGPP. CxTPS2, in contrast, showed a narrower substrate

¹⁹F NMR as a tool in chemical biology

• Diana Gimenez,
• Aoife Phelan,
• Cormac D. Murphy and
• Steven L. Cobb

Beilstein J. Org. Chem. 2021, 17, 293–318, doi:10.3762/bjoc.17.28

• -structural protein 1 (NS1A) homodimer (Figure 9) [64]. Protein NS1A is a highly conserved virulence factor from influenza virus (H3N2) comprised of an N-terminal double-stranded RNA (dsRNA)-binding domain (RBD) and a multifunctional C-terminal effector domain (ED), each of which can independently form

The preparation and properties of 1,1-difluorocyclopropane derivatives

• Kymbat S. Adekenova,
• Peter B. Wyatt and
• Sergazy M. Adekenov

Beilstein J. Org. Chem. 2021, 17, 245–272, doi:10.3762/bjoc.17.25

Supramolecular polymerization of sulfated dendritic peptide amphiphiles into multivalent L-selectin binders

• David Straßburger,
• Svenja Herziger,
• Katharina Huth,
• Moritz Urschbach,
• Rainer Haag and
• Pol Besenius

Beilstein J. Org. Chem. 2021, 17, 97–104, doi:10.3762/bjoc.17.10

• applicable platform to prepare and evaluate anti-inflammatory materials using multicomponent and multifunctional supramolecular subunits. Analysis of the self-assembly behavior of I by A: CD-spectra of 5, 10, 25 or 50 µM aqueous solutions; B, and C: TEM micrographs of negatively stained 25 µM solutions in

Et₃N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties

• Dharmender Singh,
• Vipin Kumar and
• Virender Singh

Beilstein J. Org. Chem. 2020, 16, 1740–1753, doi:10.3762/bjoc.16.146

• incorporation of sulfur to generate multifunctional β-carboline-linked benzothiophenones in good to excellent yields. The synthetic strategy could also be extended towards the synthesis of β-carboline-linked benzothiophenes. Moreover, the afforded products emerged as promising fluorophores and displayed

Nonenzymatic synthesis of anomerically pure, mannosyl-based molecular probes for scramblase identification studies

• Giovanni Picca,
• Markus Probst,
• Simon M. Langenegger,
• Oleg Khorev,
• Peter Bütikofer,
• Anant K. Menon and
• Robert Häner

Beilstein J. Org. Chem. 2020, 16, 1732–1739, doi:10.3762/bjoc.16.145

• glycolipid analogs; scramblase; Introduction Mannosyl phosphoryl dolichol (MPD), an important, multifunctional glycolipid, is used as a mannose donor for protein N-glycosylation, O- and C-mannosylation, and glycosylphosphatidylinositol (GPI) anchoring in the luminal leaflet of the endoplasmic reticulum (ER

Mechanochemical green synthesis of hyper-crosslinked cyclodextrin polymers

• Alberto Rubin Pedrazzo,
• Fabrizio Caldera,
• Marco Zanetti,
• Silvia Lucia Appleton,
• Nilesh Kumar Dhakar and
• Francesco Trotta

Beilstein J. Org. Chem. 2020, 16, 1554–1563, doi:10.3762/bjoc.16.127

• crosslinked polymers made up of cyclodextrins. The reactive hydroxy groups of CDs allow them to act as multifunctional monomers capable of crosslinking to bi- or multifunctional chemicals. The most common NS synthetic pathway consists in dissolving the chosen CD and an appropriate crosslinker in organic polar

• allow them to act as polyfunctional monomers, permitting the crosslinking with bi- or multifunctional chemicals, such as dianhydrides, diisocyanates, diepoxides, and dicarboxylic acids, etc. The polarity and size of the polymer network can be easily tuned by varying the type of the crosslinker and

Synthesis of novel multifunctional carbazole-based molecules and their thermal, electrochemical and optical properties

• Nuray Altinolcek,
• Ahmet Battal,
• Mustafa Tavasli,
• William J. Peveler,
• Holly A. Yu and
• Peter J. Skabara

Beilstein J. Org. Chem. 2020, 16, 1066–1074, doi:10.3762/bjoc.16.93

• [21][22][23]. Research continues on carbazole derivatives to find new materials with novel properties. It is therefore essential that one should design a molecule that has multifunctional usage in many different areas of technology [24]. Since carbazole is a relatively inexpensive material with unique

Recent applications of porphyrins as photocatalysts in organic synthesis: batch and continuous flow approaches

• Rodrigo Costa e Silva,
• Luely Oliveira da Silva,
• Aloisio de Andrade Bartolomeu,
• Timothy John Brocksom and
• Kleber Thiago de Oliveira

Beilstein J. Org. Chem. 2020, 16, 917–955, doi:10.3762/bjoc.16.83

• studies on this reaction are ongoing with initial suggestions of the coupling between the sulfonyl radical and the radical alkene as a key step for this transformation. In 2019, Ghaffari-Moghaddam, Oveisi and co-workers reported the synthesis of a new multifunctional MOF, namely Fe@PCN-222(Fe), and its