Article
Chemistry, Multidisciplinary
Shivam A. A. Meena, Poonam Sharma, Akhilesh K. K. Verma
Summary: A transition-metal-free one-pot synthesis of di-functionalized succinimides has been developed, which involves a radical cascade seleno/thiosulfonation of aza-1,6-enynes in an atom economical manner. This method allows the synthesis of highly decorated succinimides with excellent stereoselectivity under mild reaction conditions. The proposed radical pathway is well supported by control experiments. The reaction demonstrates advantageous features including operational simplicity, atom economy, and broad substrate scope.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Pengbo Zhang, Guo Yu, Ning Zhao, Shanshan Zhang, Minghui Zhang, Longyu Wang, Zhaoting Li, Jianxi Ying, Xia Gao
Summary: The Pd-catalyzed difluoroalkylation/cyclization/phosphinoylation reaction successfully allows the formation of C-sp3-C-F2, C-sp3-C-sp2, and C-sp2-P(O) bonds in one step, providing a straightforward route to difluoroalkyl-containing tetrasubstituted alkenylphosphine oxides with complete stereoselectivities under mild conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Hongjian Liu, Chaorong Qi, Lu Wang, Yanhui Guo, Dan Li, Huanfeng Jiang
Summary: A novel base-promoted three-component cascade reaction has been developed for the efficient synthesis of structurally diverse 2-alkyloxy-1H-pyrrole-3-carbonitrile derivatives. The reaction involves the formation of three different bonds in a single step and shows good regioselectivity depending on the structure of the alpha-hydroxy ketones used. The method features easily available starting materials, wide substrate scope, good functional group tolerance, operational simplicity, and high atom economy.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Shangyuan Wang, Jiangjie Zhang, Jian-Shu Wang, Jun Ying, Xiao-Feng Wu
Summary: A palladium-catalyzed cascade radical cyclization and carbonylation reaction of 1,7-enynes with perfluoroalkyl iodides and alcohols has been developed. The use of benzene-1,3,5-triyl triformate (TFBen) as the CO source enables the construction of 3,4-dihydroquinolin-2(1H)-one skeletons with the incorporation of both perfluoroalkyl and carbonyl units. This method provides a facile and efficient approach for the synthesis of various 3,4-dihydroquinolin-2(1H)-one derivatives with moderate to high yields and excellent E/Z selectivity.
Article
Chemistry, Organic
Chunxiang Pan, Gaowei Wang, Hengyuan Zhao, Jianxiao Ni, Ruifeng Fan, Yongyun Zhou, Yuanbin Zhu, Shiyuan Wu, Baomin Fan
Summary: An efficient stereoselective cobalt-catalyzed hydrovinylative cyclization of 1,6-enynes with chalcones to obtain functionalized pyrrolidines has been developed. The products were furnished in good yields with up to 93% ee. A plausible mechanism through which the transformation was initiated by cyclization of 1,6-enynes is proposed.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Zhengtian Ding, Yiming Wang, Wenfeng Liu, Yate Chen, Wangqing Kong
Summary: The study presents an unprecedented nickel-catalyzed one-pot synthesis of enantioenriched spiroindanones from readily available 1,6-enynes and o-formylarylboronic acids. The reaction proceeds smoothly under redox-neutral conditions, demonstrating excellent regio-, enantio-, and diastereoselectivity with a broad substrate scope.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Yan Zhang, Zhenzhi Cai, Chunhang Zhao, Hanliang Zheng, Lutz Ackermann
Summary: Electrooxidative radical cascade cyclization of 1,6-enynes enables the synthesis of sulfonamides with medium-sized rings. The activation barrier difference between alkynyl and alkenyl moieties allows for chemo-selective addition and regioselective ring formation. This metal-free and chemical oxidant-free reaction provides efficient access to sulfonamides with bridged or fused ring systems.
Article
Chemistry, Organic
Raju Jannapu Reddy, Jangam Jagadesh Kumar, Arram Haritha Kumari
Summary: A base-mediated one-pot reaction involving oxaMichael addition-elimination, cycloisomerization, and stereoselective sulfonyl migration has been developed for the synthesis of vinyl sulfonetethered chromenes. The reaction exhibited good functional group compatibility and gram-scale robustness, and the corresponding postsynthetic transformations were successful. Plausible mechanistic pathways were proposed based on experimental results.
Article
Chemistry, Organic
Ruyu Xie, Rui Li, Qingzheng Zhao, Yongxing Zhao, Jinzhong Yao, Maozhong Miao
Summary: The metal-free cyclization of allenyl ketones and p-toluenesulfonylmethyl isocyanide (TosMIC), promoted by Cs2CO3, provides a convenient access to tetrasubstituted pyrroles in which an acyl group undergoes 1,2-migration. This tandem Michael addition/annulative migration synthetic strategy is general and high-yielding for various substituted allenyl ketones. Moreover, a phosphoryl or ester moiety is also a suitable functionality to enable such migration.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Yang Li, Yongzhuang Wang, Xiaoli Huang, Yan Shi, Yuhai Tang, Jiao Jiao, Jing Li, Silong Xu
Summary: This highly efficient cascade cyclization reaction features a Ru(II)-catalyzed C-H activation initiated indole formation/Diels-Alder reaction/iminium ion cyclization sequence, providing hexacyclic indolines as single diastereomer in good to excellent yields with a broad substrate scope under mild conditions. The reaction allows for the simultaneous generation of five new chemical bonds and four new rings in one pot, offering a rapid and concise approach toward synthesizing polycyclic indoline alkaloids and their analogues.
Article
Chemistry, Multidisciplinary
You-lu Pan, Xiao-meng Gong, Rong-rong Hao, Shen-xin Zeng, Zheng-rong Shen, Wen-hai Huang
Summary: A facile CuBr2 induced radical relay addition/cyclization reaction has been developed for the synthesis of a broad range of sulfonated compounds. Some of the synthesized compounds exhibited bioactivity against cancer cell lines. This protocol offers advantages of low-cost, base-free, simple operation, and broad functional group tolerance.
Article
Chemistry, Organic
Zhi-Qing He, Shu-Jie Chen, Guo-Shu Chen, Jin-Hao Lin, Jia-Ming Wu, Yun-Lin Liu
Summary: A base-controlled divergent cyclization between 2-mercaptobenzimidazoles and beta-CF3-1,3-enynes has been developed, leading to the synthesis of either trifluoromethylated or fluorinated benzo-[4,5]-imidazo-[2,1-b]-[1,3]-thiazines. This methodology showcases its synthetic utility through a variety of downstream derivatizations.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Zhou Jin, Yun Cai, Zhengwen Wang, Hongwei Jin, Yunkui Liu, Bingwei Zhou
Summary: This study describes a nickel-catalyzed cascade hydrosilylation/cyclization reaction of 1,7-enynes with bulky triphenylsilane, resulting in a series of silyl-containing quinolinone derivatives in good to excellent yields under mild reaction conditions. The reaction exhibits excellent chemoselectivity, broad functional group tolerance, and is applicable for gram-scale synthesis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Tao Liu, Tuanli Yao, Ruihua Guo, Xiangyang Qin
Summary: A palladium-catalyzed cascade reaction was developed for the synthesis of tetrahydro-beta-carbolines and other polycyclic indoles from 2-(hydroxyenyl)sulfonanilides by combining Pd(ii)-catalyzed cyclization of alkynes and intramolecular redox-relay Heck arylation of alkenols. This method allows the construction of two rings and installation of a remote carbonyl group in a single operation, offering broad synthetic utility for further elaborations.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Inorganic & Nuclear
Jorge Escorihuela, Lawrence M. Wolf
Summary: This study investigates the mechanism and reactivity of the Pauson-Khand reaction of fluorinated and asymmetric N-tethered 1,7-enynes using density functional theory calculations. The results reveal that the intramolecular alkene insertion into the carbon-cobalt bond is the rate determining step, and the stereoselectivity is rationalized by different transition states.
Article
Chemistry, Organic
Mani Sengoden, Ryo Irie, Tharmalingam Punniyamurthy
JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Vanaparthi Satheesh, Mani Sengoden, Tharmalingam Punniyamurthy
JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Mani Sengoden, Abhisikta Bhowmick, Tharmalingam Punniyamurthy
Article
Chemistry, Organic
Ganesan Bharathiraja, Sekarpandi Sakthivel, Mani Sengoden, Tharmalingam Punniyamurthy
Article
Chemistry, Multidisciplinary
Mani Sengoden, Tharmalingam Punniyamurthy
Article
Chemistry, Multidisciplinary
Mani Sengoden, Murugan Vijay, Emayavaramban Balakumar, Tharmalingam Punniyamurthy
Article
Chemistry, Organic
Dinabandhu Sar, Rajesh Paul, Mani Sengoden, Tharmalingam Punniyamurthy
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2014)
Article
Chemistry, Multidisciplinary
Mani Sengoden, Michael North, Adrian C. Whitwood
Article
Chemistry, Multidisciplinary
Mani Sengoden, Gulzar A. Bhat, Donald J. Darensbourg
Summary: Polymers obtained from renewable monomers have attracted attention for their ability to address environmental issues and depletion of fossil fuels. In this study, a renewable eugenol-based epoxide was synthesized and its reactions with CO2, COS, and CS2 were examined. It was found that eugenol epoxide preferentially formed cyclic products with CO2 and CS2, while reacting with COS resulted in the regioselective formation of polymonothiocarbonate polymers at room temperature. The molecular structures of the renewable monomers and their cyclic products were determined using single crystal X-ray diffraction studies. Thermal gravimetric analysis and differential scanning calorimetry revealed that the polymonothiocarbonate polymers were stable up to 200 degrees C and had high glass transition temperatures.
Article
Chemistry, Multidisciplinary
Mani Sengoden, Gulzar A. Bhat, Donald J. Darensbourg
Summary: Recent years have seen significant research efforts in the development of metal-free organocatalysts for coupling reactions of CO2 and epoxides. In this study, a series of boron-phosphonium organocatalysts were synthesized and characterized for catalyzing these reactions. The catalysts exhibited high selectivity and were found to be less hygroscopic compared to metal-based catalysts. They successfully facilitated the copolymerization of CO2 and epoxides to form polycarbonates.
Review
Chemistry, Multidisciplinary
Katie J. Lamb, Ian D. Ingram, Michael North, Mani Sengoden
CURRENT GREEN CHEMISTRY
(2019)
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)
