Article
Chemistry, Multidisciplinary
Mikus Purins, Lucas Eichenberger, Jerome Waser
Summary: We present a mild approach for the synthesis of propargyl silanes from terminal alkynes. A bromonaphthyl-substituted silane was used as a silylmethyl electrophile surrogate, which underwent an aryl-to-alkyl Pd-migration followed by a Sonogashira reaction. A total of 27 propargyl silanes were obtained with yields up to 88%. The resulting products serve as versatile building blocks for addition reactions with electrophiles, triple bond hydrogenation, or silyl group cleavage with acid or fluoride sources.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Hongbo Qi, Shuai Xu, Ruiguo Zhao, Shufeng Chen
Summary: A convenient and mild method for the synthesis of ynones via NIS-mediated oxidation of propargyl alcohols has been described. The reaction provides ynones with a variety of functional groups in moderate to excellent yields, and the flexibility of this method has been demonstrated through gram-scale experiment and further transformation.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Aleksa Milosavljevic, Connor Holt, Alison J. Frontier
Summary: Herein, a one-pot nitrogen-interrupted halo-Prins/halo-Nazarov coupling cascade is reported, which enables the synthesis of functionalized cyclopenta[b]indolines with up to four contiguous stereocenters by joining an enyne and a carbonyl partner. A general method for alkynyl halo-Prins reaction of ketones is provided for the first time, allowing the formation of quaternary stereocenters. The outcomes of secondary alcohol enyne couplings and the impact of aniline enyne substituents on the reaction are also described.
Article
Chemistry, Multidisciplinary
Fa-Jie Chen, Zhenguo Hua, Jianhui Chen, Jiajia Chen, Daesung Lee, Yuanzhi Xia
Summary: This method involves the synthesis of (Z)-beta-halovinyl ketones through a one-pot Sonogashira coupling and hydrohalogenation reaction using a palladium-copper catalyst and Bronsted acid. It allows for the direct conversion of ynone intermediates to the desired product without the need for an external halogen source, resulting in high yields and good to excellent stereoselectivity.
FRONTIERS IN CHEMISTRY
(2021)
Article
Chemistry, Organic
Xiaoqin Ning, Yongke Chen, Fangdong Hu, Ying Xia
Summary: This study presents the palladium-catalyzed cross-coupling reactions of cyclobutanone-derived N-sulfonylhydrazones with aryl or benzyl halides, demonstrating that the metal carbene process and beta-hydride elimination can occur smoothly in strained ring systems to yield structurally diverse products. The preliminary success in asymmetric carbene coupling reactions in strained ring systems offers a promising route for the synthesis of enantioenriched four-membered-ring molecules.
Article
Chemistry, Organic
Genlai Zhou, Jingwen Su, Tianbo Shang, Xiaojuan Wang, Yihui Bai, Zheliang Yuan, Gangguo Zhu
Summary: A novel transformation of N-allyl ynamides was developed, enabling the synthesis of nitrogen-fused tricyclic compounds under mild reaction conditions through cascade reactions. This represents a rare example of 4-exo-dig radical cyclization, providing a new opportunity for the construction of synthetically appealing azetidines from readily available N-allyl ynamides.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Leila Kamrani Tamardash, Mohammad Bakherad, Ali Keivanloo, Behrouz Notash
Summary: An efficient method for synthesizing new pyrazole-linked oxazoles through a palladium-catalyzed Sonogashira coupling reaction was developed. Pyrazole-linked oxazole derivatives and 5-chloro-3-methyl-1-phenyl-N-(3-arylprop-2-yn-1-yl)-1H-pyrazole-4-carboxamide derivatives were obtained from the reaction of 5-chloro-3-methyl-1-phenyl-N-(prop-2-phenyl)-1H-pyrazole-4-carboxamide with aryl iodides having nitro group and aryl iodides with electron-donating groups, respectively. The prepared products were characterized using FT-IR, (HNMR)-H-1, and (CNMR)-C-13 spectroscopies.
Article
Chemistry, Applied
Lyudmila A. Grishchenko, Lidiya N. Parshina, Lyudmila I. Larina, Yana A. Kostyro, Boris A. Trofimov
Summary: New salicylate derivatives of arabinogalactan have been synthesized with high yield, showing high anti-coagulation activity. The reaction yield varies depending on the base used, and unexpected additional reactions were observed in the presence of piperidine.
CARBOHYDRATE POLYMERS
(2021)
Article
Chemistry, Organic
Debashish Mishra, Sauvik Kashyap, Prodeep Phukan
Summary: A cascade protocol for the synthesis of aminotetrazoles has been developed, achieving excellent yields and broad substrate scope without the use of any metals. The reaction proceeds via an isolable carbodiimide intermediate and intermolecular cyclization, providing 5-aminotetrazoles in a short reaction time.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Nengneng Zhou, Ziqin Xia, Sixin Wu, Kaimo Kuang, Qiankun Xu, Man Zhang
Summary: A visible-light-induced cascade cyanoalkylsulfonylation/cyclization/aromatization reaction has been developed for the construction of cyanoalkylsulfonylated quinolines, with mild reaction conditions, broad substrate scope, and excellent functional group compatibility. This cascade transformation provides a convenient route towards cyanoalkylsulfonylated quinolines by forming a C-C bond and two C-S bonds in one step.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jessica C. Bieniek, Michele Gruenewald, Johannes Winter, Dieter Schollmeyer, Siegfried R. Waldvogel
Summary: The use of electricity as a traceless oxidant provides a sustainable and novel approach to synthesize N,N'-disubstituted indazolin-3-ones through an intramolecular anodic dehydrogenative N-N coupling reaction. This method offers mild reaction conditions, easy experimental setup, excellent scalability, and high atom economy. Various indazolin-3-one derivatives were synthesized with yields up to 78% using inexpensive and sustainable electrode materials and a low supporting electrolyte concentration. Mechanistic studies suggest a biradical pathway and the cleavage of protecting group can be used to access single 2-aryl substituted indazolin-3-ones.
Article
Chemistry, Organic
Weiwei Gao, Xiaodong Wang, Linbin Yao, Bencan Tang, Guohao Mu, Tao Shi, Zhen Wang
Summary: An isomer of lycoplanine A was synthesized with a unique tetracyclic skeleton, and detailed DFT calculations were conducted to explain the selectivity in the reaction. This study may provide valuable experience for the total synthesis of lycoplanine A and other alkaloids with similar spiro-N,O-acetal cores.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Peng Zhao, Zi Zeng, Xiaoming Feng, Xiaohua Liu
Summary: The cascade reactions of alkyl alpha-diazoesters and ynones using Al(OTf)(3) as the catalyst lead to the formation of a series of 4-substituted pyrazoles. Deuterium labelling experiments, kinetic studies, and control experiments were conducted to elucidate the mechanism of the reaction. (C) 2020 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Demao Chen, Liyun Zhou, Yunyun Liu, Jie-Ping Wan
Summary: The direct three-component reactions of enaminones, aryl hydrazine hydrochlorides, and internal alkynes via Rh(iii) catalysis have enabled the synthesis of N-naphthyl pyrazoles. The use of simple substrates in these synthetic reactions results in the simultaneous construction of dual cyclic moieties, including a pyrazole ring and a phenyl ring, through the sequential formation of two C-N and three C-C bonds.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Yu Nie, Junrui Zhou, Youliang Wang
Summary: A new series of catalyst-controlled divergent cycloisomerizations of indole-tethered alkynes was developed using N-propargyl indoles as substrates and BrettPhosAuNTf(2) and PtCl4 as catalysts. The chemodivergence was attributed to the steric and electronic nature of the catalysts. A wide range of N-propargyl indoles could be used in this protocol, allowing for the divergent synthesis of 9H-pyrrolo[1,2-a]indoles and 4H-pyrrolo[3,2,1-ij]quinolines. The reactions could also be performed at mmol scales.
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)