Article
Chemistry, Organic
Atul Kumar, Gulenur N. Khatun, Rodney A. Fernandes
Summary: An efficient, mild, and economical approach for the regioselective synthesis of 4-aryl/alkyl-1-peroxy-but-3-en-2-ols from 1-substituted-1,3-butadienes using hydroperoxides and catalyzed by TBAI has been achieved. This method is simple to operate, does not require dry conditions, and has excellent tolerance to a wide range of substrates, resulting in good yields of corresponding hydroxyperoxidates. Thus, an outstanding regioselective orthogonal dioxygenation in a diene system has been accomplished.
Article
Chemistry, Organic
Xiuwen Jia, Liping Luo, Chunxi Huang, Xuemei Zhang, Zhong Lian
Summary: An iron-catalyzed four-component sulfonylthiocyanation reaction has been demonstrated, providing a feasible method for the preparation of beta-thiocyanated sulfone compounds. The reaction conditions are mild, with good functional group compatibility and broad substrate scope. Preliminary mechanistic investigation suggests the involvement of a radical pathway.
Article
Chemistry, Organic
Xinchi Gong, Zhengqi Shen, Ganghu Wang, Lingling Qu, Chunyin Zhu
Summary: A carbon-supported copper nanoparticle with high catalytic activity for the synthesis of diaryl sulfones is reported. The reaction has excellent substrate universality, and the Cu-NP is believed to involve a Cu-mediated organometallic cycle.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Jin Kyu Park, Jonghoon Oh, Sunwoo Lee
Summary: The synthesis of sulfonyl fluorides via the reaction of sulfonyl hydrazides and Et3N•3HF under electrochemical conditions is reported. Various sulfonyl fluorides were obtained in good yields. n-Bu4NI was found to act as an electrolyte and a redox catalyst.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Hai-Yang Zhao, Minqi Zhou, Xingang Zhang
Summary: A palladium-catalyzed carbonylative cross-coupling of difluoroalkyl halides with alkyl-9-BBN under 1 atm of CO has been developed, showing broad substrate scope and high functional group tolerance, even towards complex pharmaceuticals. Preliminary mechanistic studies suggest a radical pathway is involved in the reaction.
Article
Chemistry, Organic
Jiaxuan Shen, Yipin Zhang, Yanjiang Yu, Manman Wang
Summary: The reported reaction utilizes organic photoredox catalysis to achieve intermolecular pyridylation/phosphinoylation of alkenes, with broad substrate scope under mild metal-free conditions, suitable for gram-scale production and modification of medicinal molecules. Mechanistic investigations indicate that triethylamine functions as both single-electron transfer (SET) and hydrogen atom transfer (HAT) agents in the reaction.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Lin Zhu, Dian Song, Yi-Han Liu, Meng-Di Chen, Xin-Ru Zhang, Meng-Yan You, Jun-Long Zhan
Summary: In this study, an Fe-catalyzed unprotected hydroxylamine mediated Heck-type coupling was developed for the regioselective synthesis of (E)-vinyl sulfones. Mechanism studies revealed the involvement of a radical process and the multiple roles of hydroxylamines as a mild oxidant and an in situ base. This transformation not only realizes C-S bond construction promoted by unprotected hydroxylamines, but also provides a practical and complementary method for the preparation of structurally important (E)-vinyl sulfones.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Ming-Shang Liu, Hai-Wu Du, Jian-Fang Cui, Wei Shu
Summary: In this study, a metal-free protocol for synthesizing aziridines and cyclopropanes using free XH2 and alkenes is presented. The method allows for direct aziridination and cyclopropanation with unprotected XH2, and offers an attractive alternative for the straightforward synthesis of these compounds from readily available starting materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Ganesh Chandra Upreti, Tavinder Singh, Sudhir Ranjan, Raju Kumar Gupta, Anand Singh
Summary: A visible-light-promoted cascade radical cyclization has been reported for the synthesis of sulfonylated benzimidazo/indolo[2,1-a]iso-quinolin-6(5H)-ones. This reaction provides a transition-metal-free and expeditious approach to sulfonylated polyaromatics. The use of sodium metabisulfite as an SO2 surrogate and the rapid generation of molecular complexity using a three-component photochemical protocol are the key features of this reaction.
Article
Chemistry, Organic
Rongxiang Chen, Guoyang Ma, Yawen Li, Jinju Zhang, Ran Xia, Kai-Kai Wang, Lantao Liu
Summary: This study describes a mild, convenient, and effective strategy using TBAI as a catalyst to catalyze the S-H and N-H insertion reactions of alpha-diazoesters with thiophenols and aromatic amines under metal-free conditions, providing a synthetic route for various thioethers and 2-amino-2-oxoacetates in moderate to excellent yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Xiaofei Zhang, Bin Zhang, Xingwei Li
Summary: The Rh(III)-catalyzed redox-neutral C-H olefination of aryldiazenecarboxylates using arylate esters as olefinating reagents has been successfully achieved. This reaction occurs under mild and redox-neutral conditions, integrating C-H activation and transfer hydrogenation. The chemoselectivity of this reaction complements previously reported rhodium-catalyzed coupling of the same substrates.
Article
Chemistry, Organic
Weiping Xu, Terumasa Kato, Yan Liu, Akira Matsumoto, Keiji Maruoka
Summary: It has been discovered that under mild reaction conditions, two carbon-carbon bonds can be formed using vinylarenes, alkylsilyl peroxides, and beta-keto carbonyl substrates with the presence of catalytic Fe(OTf)2.
Article
Chemistry, Multidisciplinary
Mateus P. Nunes, Dhanaji V. Jawale, Fabio G. Delolo, Maria H. Araujo, Edmond Gravel, Eric Doris, Eufranio N. da Silva Junior
Summary: A heterogeneous catalyst composed of rhodium-ruthenium particles immobilized on carbon nanotubes was used in hydroboration reaction and showed high effectiveness for various alkenes and alkynes. The reactions were conducted with low catalytic loadings (0.04 mol%), solvent-free conditions, and at room temperature. Additionally, the catalyst demonstrated recyclability by being recovered through a simple centrifugation process and reused for 5 consecutive cycles without any loss in activity.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Yue Li, Xuemei Zhang, Zhong Lian
Summary: An efficient and practical method for highly regio- and stereo-selective cyanosulfonylation of allenes using sulfur dioxide has been explored. The reaction conditions are mild and the substrate compatibility is good. Interestingly, the SOgen reagent showed higher reactivity compared to other SO2 surrogates. The obtained products can be further transformed into valuable compounds. Preliminary mechanism studies suggest a radical pathway for the reaction.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Yang Gao, Yushan Cui, Yanping Huo, Jinhong Chen, Minwei She, Xianwei Li, Qian Chen, Xiao-Qiang Hu
Summary: A nickel-catalyzed polarity-reversed hydroamination of olefins has been developed, providing a convenient route to N-alkyl-2-aminobenzophenones intermediates. This method is compatible with a wide range of olefins and anthranils, delivering the desired amines in high yields, making it applicable for organic synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)