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Organic thermally activated delayed fluorescence material with strained benzoguanidine donor
We present organic TADF material (4BGIPN) based on the strained benzoguanidine donor and compare it with the benchmark carbazole-based material (4CzIPN). Extended π-conjugation in 4BGIPN material results in yellow-green luminescence at 512 nm with a fast radiative rate of 5.5 × 10−5 s−1 and a photoluminescence quantum yield of 46% in methylcyclohexane solution. Such a nitrogen-rich 4BGIPN material has a significantly stabilized highest occupied molecular orbital (HOMO) at −6.4 eV while the lowest unoccupied molecular orbital (LUMO) at −4.0 eV, indicating potential suitability for applicati...
Source: Beilstein Journal of Organic Chemistry - September 7, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: guanidine organic photoluminescence TADF yellow Full Research Paper Source Type: research

Non-noble metal-catalyzed cross-dehydrogenation coupling (CDC) involving ether α -C(sp3) – H to construct C – C bonds
Abstract Ether derivatives are widespread as essential building blocks in various drugs, natural products, agrochemicals, and materials. Modern economy requires developing green strategies with improved efficiency and reduction of waste. Due to its atom and step-economy, the cross-dehydrogenative coupling (CDC) reaction has 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 ...
Source: Beilstein Journal of Organic Chemistry - September 6, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: alkylation cross-dehydrogenation coupling ether non-noble metals Review Source Type: research

Metal catalyst-free N-allylation/alkylation of imidazole and benzimidazole with Morita – Baylis – Hillman (MBH) alcohols and acetates
Abstract A highly α-regioselective N-nucleophilic allylic substitution of cyclic MBH alcohols and acetates with imidazole or benzimidazole, in toluene at reflux with an azeotropic distillation, was successfully carried out with no catalysts or additives, affording the corresponding N-substituted imidazole derivatives in good yields. On the other hand, in refluxing toluene or methanol, the aza-Michael addition of imidazole onto acyclic MBH alcohols was performed using DABCO as an additive, leading to the corresponding 1,4-adducts in 70–84% yields. Beilstein J. Org. Chem. 2023, 19, 1251–1258. doi:10.37...
Source: Beilstein Journal of Organic Chemistry - September 1, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: allylic substitution aza-Michael addition imidazole Morita – Baylis Hillman Full Research Paper Source Type: research

Acetaldehyde in the Enders triple cascade reaction via acetaldehyde dimethyl acetal
Abstract Asymmetric organocatalyzed multicomponent reactions represent an important toolbox in the field of organic synthesis to build complex scaffolds starting from simple starting materials. The Enders three-component cascade reaction was a cornerstone in the field and a plethora of organocatalyzed cascade reactions followed. However, acetaldehyde was not shown as a successful reaction partner, probably because of its high reactivity. Herein, we report the Enders-type cascade reaction using acetaldehyde dimethyl acetal, as a masked form of acetaldehyde. This strategy directly converts acetaldehyde, nitroalkenes and enal...
Source: Beilstein Journal of Organic Chemistry - August 24, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: acetaldehyde acetaldehyde dimethyl acetal cascade reaction multicomponent reaction organocatalysis Full Research Paper Source Type: research

Selective construction of dispiro[indoline-3,2'-quinoline-3',3'' -indoline] and dispiro[indoline-3,2'-pyrrole-3',3'' -indoline] via three-component reaction
Abstract A convenient synthetic procedure for the construction of novel dispirooxindole motifs was successfully developed by base-promoted three-component reaction of ammonium acetate, isatins and in situ-generated 3-isatyl-1,4-dicarbonyl compounds. The piperidine-promoted three-component reaction of ammonium acetate, isatins and the in situ-generated dimedone adducts of 3-ethoxycarbonylmethyleneoxindoles afforded mutlifunctionalized dispiro[indoline-3,2'-quinoline-3',3''-indoline] derivatives in good yields and with high diastereoselectivity. On the other hand, a similar reaction of the dimedone adducts of...
Source: Beilstein Journal of Organic Chemistry - August 22, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: cascade reaction dimedone isatin 3-methyleneoxindole multicomponent reaction spirooxindole Full Research Paper Source Type: research

Radical ligand transfer: a general strategy for radical functionalization
Abstract The place of alkyl radicals in organic chemistry has changed markedly over the last several decades, evolving from challenging-to-generate “uncontrollable” species prone to side reactions to versatile reactive intermediates enabling construction of myriad C–C and C–X bonds. This maturation of free radical chemistry has been enabled by several advances, including the proliferation of efficient radical generation methods, such as hydrogen atom transfer (HAT), alkene addition, and decarboxylation. At least as important has been innovation in radical functionalization methods, including radical...
Source: Beilstein Journal of Organic Chemistry - August 15, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: catalysis cooperative catalysis earth abundant elements photocatalysis radicals Perspective Source Type: research

Unravelling a trichloroacetic acid-catalyzed cascade access to benzo[f]chromeno[2,3-h]quinoxalinoporphyrins
Abstract A facile one-pot four-component synthetic methodology is evolved to construct novel copper(II) benzo[f]chromeno[2,3-h]quinoxalinoporphyrins in good yields via a sequential reaction of copper(II) 2,3-diamino-5,10,15,20-tetraarylporphyrins, 2-hydroxynaphthalene-1,4-dione, aromatic aldehydes, and dimedone in the presence of a catalytic amount of trichloroacetic acid in chloroform at 65 °C. Further, the newly prepared copper(II) porphyrins were transformed to the corresponding free base and zinc(II) benzo[f]chromeno[2,3-h]quinoxalinoporphyrins under standard demetallation and zinc insertion conditions. The absorp...
Source: Beilstein Journal of Organic Chemistry - August 11, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: bathochromic shift benzo[f]chromeno[2,3-h]quinoxalinoporphyrins catalysis multicomponent synthesis one-pot reaction trichloroacetic acid Full Research Paper Source Type: research

Cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives
Abstract It was shown that the reaction of 2-cyanothioacetamides with hydrazine involves both cyano- and thioamide groups, and 3,5-diaminopyrazoles are formed. In the reaction of 2-cyano-3-(dimethylamino)-N,N-dimethylprop-2-enethioamides with hydrazine and its derivatives, the interaction proceeds with the participation of cyano- and enamine groups, not affecting the thiocarbamoyl group, and leads to the formation of 4-thiocarbamoylpyrazoles. A synthesis method has been developed and a series of 1-substituted-4-thiocarbamoyl pyrazoles has been thus synthesized. The structure of the reaction products was studied using NMR s...
Source: Beilstein Journal of Organic Chemistry - August 8, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: aminopyrazoles 2-cyanothioacetamides enamines hydrazines Full Research Paper Source Type: research

Enabling artificial photosynthesis systems with molecular recycling: A review of photo- and electrochemical methods for regenerating organic sacrificial electron donors
Abstract This review surveys advances in the literature that impact organic sacrificial electron donor recycling in artificial photosynthesis. Systems for photocatalytic carbon dioxide reduction are optimized using sacrificial electron donors. One strategy for coupling carbon dioxide reduction and water oxidation to achieve artificial photosynthesis is to use a redox mediator, or recyclable electron donor. This review highlights photo- and electrochemical methods for recycling amines and NADH analogues that can be used as electron donors in artificial photosynthesis. Important properties of sacrificial donors and recycling...
Source: Beilstein Journal of Organic Chemistry - August 8, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: artificial photosynthesis photocatalysis redox couple sacrificial electron donor solar fuels Review Source Type: research

Retraction: One-pot odourless synthesis of thioesters via in situ generation of thiobenzoic acids using benzoic anhydrides and thiourea
Beilstein J. Org. Chem. 2023, 19, 1170. doi:10.3762/bjoc.19.85 (Source: Beilstein Journal of Organic Chemistry)
Source: Beilstein Journal of Organic Chemistry - August 7, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: benzoic anhydride Michael addition nucleophilic displacement thioester thiourea Retraction Source Type: research

Exploring the role of halogen bonding in iodonium ylides: insights into unexpected reactivity and reaction control
Abstract Halogen bonding is commonly found with iodine-containing molecules, and it arises when Lewis bases interact with iodine’s σ-holes. Halogen bonding and σ-holes have been encountered in numerous monovalent and hypervalent iodine-containing compounds, and in 2022 σ-holes were computationally confirmed and quantified in the iodonium ylide subset of hypervalent iodine compounds. In light of this new discovery, this article provides an overview of the reactions of iodonium ylides in which halogen bonding has been invoked. Herein, we summarize key discoveries and mechanistic proposals from the early ...
Source: Beilstein Journal of Organic Chemistry - August 7, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: electron donor – acceptor complex halogen bonding σ -holes iodonium ylides ortho-effect Review Source Type: research

New one-pot synthesis of 4-arylpyrazolo[3,4-b]pyridin-6-ones based on 5-aminopyrazoles and azlactones
Abstract An effective one-pot strategy was developed for the synthesis of 4-arylpyrazolo[3,4-b]pyridin-6-ones from pyrazolo[3,4-b]pyridin-6-ones, obtained by reacting 5-aminopyrazoles with 4-arylidene-2-phenyloxazol-5(4H)-ones (azlactones) under solvent-free conditions, through subsequent elimination of a benzamide molecule in a superbasic medium (t-BuOK/DMSO). The fluorescent properties of the synthesized compounds were studied. 4-Arylpyrazolo[3,4-b]pyridin-6-ones luminesce in the region of 409–440 nm with a quantum yield of 0.09–0.23 when irradiated with UV light. Beilstein J. Org. Chem. 2023, 19, 1155–...
Source: Beilstein Journal of Organic Chemistry - August 2, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: 5-aminopyrazole azlactone elimination fluorescence one-pot synthesis pyrazolo[3,4-b]pyridin-6-one Full Research Paper Source Type: research

Two new lanostanoid glycosides isolated from a Kenyan polypore Fomitopsis carnea
Abstract Chemical exploration of solid-state cultures of the polypore Fomitopsis carnea afforded two new C31 lanostane-type triterpenoid glycosides, forpiniosides B (1) and C (2) together with two known derivatives, namely 3-epipachymic acid (3) and (3α,25S)-3-O-malonyl-23-oxolanost-8,24(31)-dien-26-oic acid (4). The structures of the isolated compounds were established based on HRESIMS and extensive 1D and 2D NMR experiments. All the isolated compounds were assessed for their antimicrobial and cytotoxic activities. Among the tested compounds, forpinioside B (1) exhibited significant antimicrobial activity against Sta...
Source: Beilstein Journal of Organic Chemistry - August 2, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: antimicrobial activity Fomitopsis carnea lanostane glycosides Polyporales Full Research Paper Source Type: research

Selective and scalable oxygenation of heteroatoms using the elements of nature: air, water, and light
Abstract Sustainable oxidation protocols aim to provide an environmentally friendly and cost-effective method for the production of various chemicals and materials. The development of such protocols can lead to reduced energy consumption, fewer harmful byproducts, and increased efficiency in industrial processes. As such, this field of research is of great importance and interest to both academia and industry. This work showcases a sustainable and catalyst-free oxidation method for heteroatoms (e.g., S, P, and Se) using only air, water and light. An additional reaction pathway is proposed in which the incorporated oxygen o...
Source: Beilstein Journal of Organic Chemistry - July 31, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: catalyst-free flow chemistry oxygen photochemistry sustainable oxidation Full Research Paper Source Type: research

Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines via a base-induced rearrangement of functionalized imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazines
Abstract A series of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines was synthesized via a cascade sequence of hydrolysis and skeletal rearrangement of imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazin-7(8H)-ylidene)acetic acid esters in methanol upon treatment with excess KOH. Imidazo[4,5-e]thiazolo[3,2-b][1,2,4]triazin-6(7H)-ylidene)acetic acid esters are also suitable substrates for the reaction. In this case hydrolysis and thiazole ring expansion were accompanied with the change of the thiazolotriazine junction type from thiazolo[3,2-b][1,2,4]triazine to thiazino[2,3-c][1,2,4]triazine. Beilstein J. Org. Chem. 2023, 19, 1...
Source: Beilstein Journal of Organic Chemistry - July 28, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: N,S-heterocycles ring expansion skeletal rearrangement 1,3-thiazines thiazolidine-4-ones Full Research Paper Source Type: research