Article
Chemistry, Multidisciplinary
Lin-Jun Qi, Cui-Ting Li, Zheng-Qi Huang, Jia-Tian Jiang, Xin-Qi Zhu, Xin Lu, Long-Wu Ye
Summary: The study presents a novel copper-catalyzed asymmetric formal annulation reaction, which can synthesize a range of chiral oxygen-heterocycles via carbonyl ylides with excellent enantioselectivity and yields.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Yuhao Ding, Hailin Guo, Jingwen Fan, Zhiyong Li, Guolin Cheng
Summary: In this work, a method for efficient synthesis of decorated thiazolidine-4-thiones was reported, exhibiting excellent advantages in terms of chemoselectivity and yield.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Gulshan Kumar, Mithilesh Nagpure, Vajja Krishna Rao, Sankar K. Guchhait
Summary: A (4+1)-annulation reaction between arylidene heterocyclic-N-fused imidazolones and alpha-carbonyl sulfoxonium ylides has been developed, allowing the efficient synthesis of various N-heterocycle-fused furans, which are important structural components in secondary hydroxyls and drug/bioactive compounds. This study explores the unique triple-role of alpha-carbonyl sulfoxonium ylides and the characteristic stereo-electronic functional behavior of arylidene N-fused imidazolones.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Shulei Hu, Xu Han, Xiong Xie, Feifei Fang, Yong Wang, Abdusaid Saidahmatov, Hong Liu, Jiang Wang
Summary: A method for synthesizing pyrazolo[1,2-a]cinnolines was developed using rhodium(III)-catalyzed C-H activation of pyrazolidinones and subsequent [4+2] annulation of sulfoxonium ylides. By adjusting the reaction conditions, 5-substituted or 5,10-disubstituted pyrazolo[1,2-a]cinnolines could be obtained. Gram-scale synthesis and practical transformations demonstrated the feasibility of this method, which features simplified operation and readily available reactants.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Toktam S. Shirazian, Hossein Zahedian Tejeneki, Ali Nikbakht, Frank Rominger, Saeed Balalaie
Summary: This study presents a novel method for synthesizing functionalized acridines using a base-promoted formal [4+2] cycloaddition reaction. The method exhibits high selectivity and efficiency, making it a valuable approach for the synthesis of acridine backbones.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Li-Jia Liu, Ming Dai, Lei Song, Hui-Yu Chen, Ming Bian, Yu-Ning Gao, Zhen-Jiang Liu
Summary: The [2+1] annulation reaction of alpha-keto sulfur ylides and beta, gamma-unsaturated-alpha-ketoesters was studied in detail. A series of 1,2,3-trisubstituted cyclopropane derivatives were obtained with moderate to good yields and excellent diastereoselectivities through this rapid and effective reaction in only 10 minutes. The reaction condition is simple and mild without any alkali, catalyst or additive. The assistance of water in this reaction can lead to the formation of a single cyclopropane product.
Article
Chemistry, Organic
Alexander A. Fadeev, Anton S. Makarov, Olga A. Ivanova, Maxim G. Uchuskin, Igor Trushkov
Summary: The divergent synthesis of benzannulated 2,8-dioxabicyclo[3.2.1]octanes and 2,3-dihydrobenzofurans using extended Corey-Chaykovsky reactions demonstrates the potential of this method in producing products with crucially different heterocyclic skeletons from the same starting compounds.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Min Gao, Yanshu Luo, Qianlan Xu, Yukun Zhao, Xiangnan Gong, Yuanzhi Xia, Lin Hu
Summary: The research achieved a unified catalytic asymmetric (N+1) (N=4, 5) annulation reaction of oxindoles with bifunctional peroxides using a chiral phase-transfer catalyst (PTC). This method provides a distinct way to access valuable chiral spirooxindole-tetrahydrofurans and -tetrahydropyrans with good yields and high enantioselectivities under mild conditions. The DFT calculations were performed to rationalize the high enantioselectivity observed in the reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Shuaishuai Song, Yunfei Lai, Zekun Tuo, Jianming Zhong, Wang Zhou
Summary: A rhodium(III)-catalyzed oxidative cyclization of chalcones with internal alkynes is reported, resulting in the formation of biologically important 3,3-disubstituted 1-indanones and reusable aromatic aldehydes. This transformation exhibits a unique (4+1) reaction mode, excellent regioselectivity, broad substrate scope, ability to construct quaternary carbon centers, and scalability. Steric hindrance from the substrate and ligand likely controls the chemoselectivity of this carbocyclization. Importantly, this discovery enables a practical two-step protocol to switch the overall reaction from a (3+2) to a (4+1) annulation of acetophenones with internal alkynes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Song Zou, Zeyu Zhang, Chao Chen, Chanjuan Xi
Summary: This study achieved the formal [4 + 2] annulation of styrene oxides with alkynes catalyzed by MeOTf, resulting in polysubstituted naphthalenes with sequential electrophilic cyclization/ring expansion. The reaction showed high regioselectivity with satisfactory yields and could be carried out on gram scale.
CHINESE CHEMICAL LETTERS
(2022)
Review
Chemistry, Multidisciplinary
Xuling Chen, Pengfei Li
Summary: Benefiting from the rapid development of MBH reaction, the reaction of MBH adducts has become one of the most synthetically useful transformations. However, the (1+4)-annulations of MBH adducts have not developed rapidly until recently, compared with the well-established allylic alkylations and (3+2)-annulations. As a beneficial complement to the (3+2)-annulations, the (1+4)-annulations of MBH adducts provide a robust access to structurally diverse five-membered carbo- and heterocycles. This paper summarizes recent advances in organocatalytic (1+4)-annulations using MBH adducts as 1 C-synthons for the construction of functionalized five-membered carbo- and heterocycles.
Article
Chemistry, Multidisciplinary
Shreemoyee Kumar, Akshay M. Nair, Chandra M. R. Volla
Summary: In this study, two distinct pyridine N-oxide directed C-H activation protocols were developed to achieve [4+1] annulation and alkoxylation of benzamide derivatives by merging Co-catalysis with visible-light photoredox catalysis. The protocols offer good yields of the desired products under facile conditions at room temperature. The use of an inexpensive photocatalyst coupled with molecular oxygen, eliminating the need for stoichiometric oxidants, is the key highlight of this work. The protocols are scalable and allow for further modification of the products. Additionally, preliminary studies were conducted to investigate the reaction mechanism.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Organic
Fangfang Lu, Yangxu Chen, Xue Song, Chenxia Yu, Tuanjie Li, Kai Zhang, Changsheng Yao
Summary: A successful NHC-catalyzed [2+4] cyclization reaction was developed to synthesize highly substituted 4H-pyran derivatives with cheap and easily available starting materials, mild reaction conditions, moderate to excellent yields, and high atom economy.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Xing Guo, Boming Shen, Chang Liu, Hongyue Zhao, Xuechen Li, Peiyuan Yu, Pengfei Li
Summary: Based on the frontier molecular orbital theory, two types of modified enones have been designed and successfully applied in the chiral phosphine-catalyzed stereoselective [1 + 4]-annulation of MBH carbonates. The reaction proceeds smoothly under mild conditions, exhibiting excellent functional group tolerance and providing a broad scope of enantioenriched 2,3-dihydrofurans with high efficiency. DFT calculations have been used to guide the design of additional enones and understand the origin of stereoselectivity. Furthermore, this method explores the application scope of enones and enriches the chemistry of [1 + 4]-annulations of MBH carbonates for the preparation of optically active multifunctional 2,3-dihydrofurans.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Jie Cui, Tongdao Wang
Summary: A formal [4 + 1] cycloaddition reaction was developed for the synthesis of unsaturated BN-heterocycles. The reaction involved the reaction of ketiminoboranes with various isonitriles and proceeded via a hydroboration/allylboration/[4 + 1] cycloaddition reaction sequence. The in situ generation of BN-dienes through intramolecular proton transfer was supported by deuterium labelling experiments. This catalyst-free multicomponent reaction provides an efficient approach for the formation of unsaturated BN-heterocycles beyond traditional five-membered rings.
ORGANIC CHEMISTRY FRONTIERS
(2023)
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)
