Article
Chemistry, Applied
Jen-Yu Kuan, I-Ting Chen, Hsuan Lin, Jeng-Liang Han
Summary: We have developed a substrate-dependent, regio- and stereocontrolled diversity-oriented organocatalytic vinylogous Michael addition/cyclization cascade of 2-alkylidene indane-1,3-diones with enals, using secondary amines as the catalyst. This method allows for the selective synthesis of spiroindane-1,3-diones, tetrahydrofluoren-9-one derivatives, and benzofused oxabicyclo[3.3.1]nonanes. Plausible catalytic pathways have been proposed, and DFT calculations have clarified the mechanisms involved.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Koichi Kodama, Kazuhisa Maruyama, Takuji Hirose
Summary: Chiral 1,3-aminosquaramides derived from cis-2-benzamidocyclohexanecarboxylic acid were synthesized and used as bifunctional organocatalysts for asymmetric Michael addition reaction. The optimized organocatalyst achieved an enantioselectivity of up to 96% in the reaction of 1,3-diketones and 1,3-ketoesters with β-nitrostyrenes. Plausible transition state was proposed based on previous reports and DFT calculations.
Article
Crystallography
Lin Yuan, Yuan-Da Li, Xu Fan, Zhong-Yan Li
Summary: The substance is C11H14ClNO with monoclinic crystal system in space group P2(1)/c. The cell dimensions are a = 9.072 angstrom, b = 5.882 angstrom, c = 21.258 angstrom, with beta angle of 100.351 degrees, at a temperature of 296K.
ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES
(2021)
Article
Green & Sustainable Science & Technology
Fei Liu, Gary T. Rochelle, Mengxiang Fang, Tao Wang
Summary: The study investigated the volatility of DEEA and AEEA in CO2 capture, highlighting that DEEA is more volatile than MEA while AEEA is essentially non-volatile. Both experimental and modeling data provided insights into the changes in volatility and activity coefficients of the two amines under different conditions.
INTERNATIONAL JOURNAL OF GREENHOUSE GAS CONTROL
(2021)
Article
Chemistry, Organic
Yu-Xia Lu, Xue-Jiao Lv, Chang Liu, Yan-Kai Liu
Summary: This study presents the triethylamine-promoted cascade Henry reaction/elimination of HNO(2)/cyclization reaction of 2-oxoaldehydes with nitroalkanes bearing various remote functionalities. Both chiral and achiral nitroalkanes were found to be suitable for this protocol, resulting in the formation of a variety of oxacycles, including chromenes, chromanes, cyclic hemiacetals, and polycyclic acetals. Unexpected regioselective photooxygenation occurred during derivatization without a sensitizer, converting the derived diene product into a dioxetane through reaction with singlet oxygen, ultimately yielding chromen-2-one and benzaldehyde after fragmentation.
Article
Chemistry, Organic
Peng Zhu, Yi Yang, Yan Liu, Yungui Peng
Summary: A series of trifunctional BINAP-based monophosphonium phase-transfer catalysts were developed and used for the asymmetric addition of alpha-diazomethylphosphonates. The method showed high tolerance for 2-unsubstituted sulfonylindoles and achieved high enantioselectivity.
Article
Chemistry, Organic
Giacomo Mari, Matteo Corrieri, Lucia De Crescentini, Gianfranco Favi, Stefania Santeusanio, Fabio Mantellini
Summary: Substituted 1-aminopyrroles can be easily accessed through an iron-catalyzed cascade reaction of 1,2-diaza-1,3-dienes, which involves a [4+2] cyclodimerization and ring contraction process. The presence of activated hydrogen in the terminal position of the azo-enic moiety is crucial for the synthesis of pyrroles.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Shi-Jie Zhu, Zhi-Feng Hao, Ya Pan, Ying Zhou, Xiong-Li Liu, Ming Zhang, Chuan-Wen Lei
Summary: In this study, a stepwise enantioselective formal (3 + 2) cyclocondensation reaction was successfully accomplished, leading to the synthesis of spiro-fused pentacyclic spirooxindoles. The reaction showed good overall yields, excellent dr, and high ee values.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Shi-Jie Zhu, Zhi-Feng Hao, Ya Pan, Ying Zhou, Xiong-Li Liu, Ming Zhang, Chuan-Wen Lei
Summary: The first enantioselective formal (3 + 2) cyclocondensation involving alpha,fi-unsaturated pyrazoleamides as 3-carbon partners was successfully achieved in a stepwise fashion. The protocol led to the synthesis of spiro-fused pentacyclic spirooxindoles with good overall yields, excellent diastereomeric ratios, and high enantiomeric excess values.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Jiang-Song Zhai, Dong-Hua Xie, Da-Ming Du
Summary: A new synthetic method has been developed for the synthesis of chiral bispirocyclic indanone compounds through squaramide-catalyzed asymmetric Michael/cyclization tandem reaction. The obtained products were further transformed through oxidation and methylation reactions.
Article
Chemistry, Medicinal
Marcia Renio, Dina Murtinho, M. Rita Ventura
Summary: Novel 1,3-diamine-derived bifunctional thiourea and squaramide organocatalysts were successfully synthesized from (+)-camphoric acid, demonstrating flexible structure variation and efficient catalytic activity.
Article
Chemistry, Multidisciplinary
Mohammad F. Rahman, Ikuhide Fujisawa, Naoki Haraguchi, Shinichi Itsuno
Summary: This article reports on chiral cinchona alkaloid-derived polymers as catalysts in the asymmetric aza-Michael reaction between aniline and chalcone. These polymers showed excellent catalytic performance, yielding chiral β-amino ketones in a highly enantioselective manner (up to >99% ee) under solvent-free conditions. The insolubility of the polymer catalyst facilitated its separation from the reaction mixture, and it could be reused multiple times without any loss of catalytic performance.
Article
Crystallography
Qian-Zhi Yang, Yu-Xin Yang, Jin-Hao Kuang, Zhong-Yan Li, Lin Yuan
Summary: This is the crystal structure parameters of an organic compound. It belongs to the monoclinic system with the cell parameters a = 10.488(7) ångström, b = 10.139(7) ångström, c = 22.760(15) ångström, β = 99.705 degrees. The volume is determined to be 2386(3) ångström(3), and there are four molecules in the unit cell.
ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES
(2022)
Article
Chemistry, Organic
Rayhan G. Biswas, Sumit K. Ray, Rajshekhar A. Unhale, Vinod K. Singh
Summary: A bifunctional urea catalyzed cascade reaction of 5-alkenyl thiazolones and monofluorinated beta-diketones, derived from quinine, has been developed, yielding fluorine containing 4-acyloxy thiazoles with high yields and good diastereo- and excellent enantioselectivities. Synthetic transformations, including the synthesis of 4-hydroxy thiazoles, have been successfully demonstrated.
Article
Chemistry, Organic
Yinsong Wu, Xinwei He, Mengqing Xie, Ruxue Li, Yi Ning, Jiahui Duan, Enshen Zhang, Yongjia Shang
Summary: The Rh(III)-catalyzed cascade nucleophilic addition/intramolecular annulation of 2-diazo-1,3-diketones with 1,3-dicarbonyl compounds has been successfully achieved to yield 6,7-dihydrobenzofuran-4(5H)-ones in up to 91% yields. The reaction tolerates a wide range of substrates and functional groups under optimized conditions and is scalable and adaptable to late-stage functionalization.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Houaria Bendjedou, Filippo Maggi, Malika Bennaceur, Michele Mancinelli, Houari Benamar, Luciano Barboni
Summary: In this study, a new compound and three known compounds were isolated from L. intricatum for the first time. Chromatographic techniques were used to isolate compounds 1-4 from the leaf extract, and the structure of compound 1 was fully elucidated through NMR, MS, and ECD experiments.
NATURAL PRODUCT RESEARCH
(2022)
Article
Chemistry, Multidisciplinary
Minjeong Lee, Seungjae Yun, Dongil Ho, Taeshik Earmme, Assunta Marrocchi, Luigi Vaccaro, Choongik Kim
Summary: This study successfully demonstrated the use of sustainable green solvents in the fabrication of organic semiconductor devices, showing promising results in terms of device performance and transfer gain. The devices fabricated using green solvents exhibited typical ambipolar characteristics and decent transfer gain, indicating the potential application of green solvents in the manufacture of organic semiconductor devices.
JOURNAL OF INDUSTRIAL AND ENGINEERING CHEMISTRY
(2022)
Article
Chemistry, Organic
Di Hao, Zhen Yang, Yali Liu, Yang Li, Chuntian Li, Yanlong Gu, Luigi Vaccaro, Jichang Liu, Ping Liu
Summary: An efficient Pd-catalyzed direct C-H arylation of pyrrolo[1,2-a]quinoxalines with aryl iodides has been developed, providing a selective route to a series of 1-arylated and 1,3-diarylated pyrrolo[1,2-a]quinoxalines with good yields. The method features broad substrate scope, good functional group tolerance, and gram-scale synthesis capability. Additionally, C3-thiocyanation of the arylated product has been achieved, indicating potential applications in organic synthesis and medicinal chemistry.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Yang Li, Yali Liu, Di Hao, Chuntian Li, Yan Liu, Yanlong Gu, Luigi Vaccaro, Ping Liu
Summary: An efficient Cu(II)-catalyzed direct C-H trifluoromethylation of pyrrolo[1,2-a]quinoxalines with CF3SO2Na in the presence of K2S2O8 has been developed. The reaction provides a variety of C1-trifluoromethylated pyrrolo[1,2-a]quinoxaline products in moderate to good yields. This method demonstrates broad substrate scope, excellent regioselectivity, and gram-scale synthesis.
Article
Chemistry, Physical
Xuezhen Li, Jing He, Mingxi Du, Jie Zhang, Yanlong Gu, Luigi Vaccaro, Ping Liu
Summary: An efficient I-2/K2S2O8-promoted ring expansion of benzo[d]thiazole and 3-oxo-3-arylpropanenitrile was developed, yielding diverse 3-aryl-4H-benzo[b][1,4]thiazine-2-carbonitriles in moderate to excellent yields. The protocol is characterized by metal-free reaction conditions, stable starting materials, and good group tolerance. Mechanistic studies suggest the reaction may proceed via a free radical process.
MOLECULAR CATALYSIS
(2022)
Article
Biochemistry & Molecular Biology
Bienvenu Tsakem, Paul Eckhardt, Roland Tchuenteu Tchuenguem, Beaudelaire Kemvoufo Ponou, Jean Paul Dzoyem, Remy Bertrand Teponno, Till Opatz, Luciano Barboni, Leon Azefack Tapondjou
Summary: A new friedelane triterpenoid and sixteen previously reported compounds were isolated from the ethanol extract of Phyllanthus muellerianus leaves. Their structures were identified using spectroscopy and comparison to literature data. Some isolated compounds and the extract showed high antioxidant and antimicrobial activities.
BIOCHEMICAL SYSTEMATICS AND ECOLOGY
(2022)
Article
Plant Sciences
Robert V. Kepdieu Tchebou, Paul Eckhardt, Blondelle Matio Kemkuignou, Roland Tchuenguem, Romuald Tematio Fouedjou, Beaudelaire Kemvoufo Ponou, Jean Paul Dzoyem, Remy Bertrand Teponno, Luciano Barboni, Till Opatz, Leon Azefack Tapondjou
Summary: In this study, a new dinorcassane-type diterpenoid and a new steroidal saponin were isolated from the stem barks of Distemonanthus benthamianus in Cameroon. Antimicrobial screening showed significant inhibition only for the n-butanol fraction against Candida albicans and Candida glabrata.
PHYTOCHEMISTRY LETTERS
(2022)
Review
Chemistry, Physical
Federica Valentini, Assunta Marrocchi, Luigi Vaccaro
Summary: Liquid organic hydrogen carriers (LOHCs) are attractive materials that can generate hydrogen on site for the production of biofuel precursors, fuels, or fuel additives. This comprehensive review article provides an overview of the hydrogen transfer mechanisms for different LOHCs and discusses the importance of catalyst design and reaction condition selection.
ADVANCED ENERGY MATERIALS
(2022)
Article
Chemistry, Applied
Isaac Nde Chedjou, Francis Tatong Ngouafong, Roland Tchuenteu Tchuenguem, Jean Paul Dzoyem, Beaudelaire Kemvoufo Ponou, Remy Bertrand Teponno, Luciano Barboni, Leon Azefack Tapondjou
Summary: Phytochemical investigation of the methanol extracts from the leaves and bark of Senna siamea led to the discovery of a new flavone C-glycoside and sixteen known compounds. Some of the isolated compounds exhibited antimicrobial properties.
NATURAL PRODUCT RESEARCH
(2023)
Article
Chemistry, Organic
Tian Sang, Chuntian Li, Fan Jia, Jing He, Yan Liu, Luigi Vaccaro, Jichang Liu, Ping Liu
Summary: This study has developed a series of halogenated systems for pyrazolo[1,5-a]pyrimidines, achieving selective transformations by mono- and di-iodination using varying ratios of pyrazolo[1,5-a]pyrimidines and NIS. Additionally, the reaction with NBS or NCS produces unique dibrominated or dichlorinated products. The wide range of substrates, good functional group tolerance, and gram-scale synthesis demonstrate the potential application of this reaction.
POLYCYCLIC AROMATIC COMPOUNDS
(2023)
Review
Chemistry, Physical
Federica Valentini, Oriana Piermatti, Luigi Vaccaro
Summary: The direct functionalization of inactivated C-H bonds has gained attention as a method for step-economy, atom-efficient, and environmentally sustainable processes. The design and preparation of highly active metal nanoparticles as catalysts for C-H bond activation under mild reaction conditions is still being investigated. This review focuses on the functionalization of un-activated C(sp3)-H, C(sp2)-H, and C(sp)-H bonds using metal and metal oxide nanoparticles for C-O and C-X (X = Halogen, B, P, S, Se) bond formation, leading to more sustainable access to industrial production.
Review
Chemistry, Multidisciplinary
Dario Marchionni, Sumon Basak, Alireza Nazari Khodadadi, Assunta Marrocchi, Luigi Vaccaro
Summary: The past decade has witnessed a renewed interest in borazines and BN-doped polycyclic aromatic hydrocarbons due to their potential in various applications. This review critically examines the synthesis methods of (substituted) B3N3 motifs and focuses on the discussion of borazine-doped carbon structures developed for materials science applications.
ADVANCED FUNCTIONAL MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Nihad Salameh, Federica Valentini, Olivier Baudoin, Luigi Vaccaro
Summary: We report a general and efficient enantioselective C-H arylation of aryl bromides using BozPhos as the bisphosphine ligand and SP-NHC-PdII as recoverable heterogeneous catalyst. By exploiting the release and catch mechanism of action, high enantioselectivities were achieved across different substrates containing methyl, cyclopropyl and aryl C-H bonds. The developed catalytic system provides a more sustainable solution for the synthesis of high added-value chiral products through recycling of the precious metal.
Article
Chemistry, Multidisciplinary
Giulia Brufani, Federica Valentini, Gabriele Rossini, Lucia Rosignoli, Yanlong Gu, Ping Liu, Luigi Vaccaro
Summary: Metal contamination is a significant problem in chemical synthesis, especially for products with biological activity. The use of appropriate operating conditions, such as a copper tube flow reactor (CTFR), can greatly reduce metal leaching and waste generation. A waste-minimized continuous flow process for synthesizing 1,4-disubstituted β-keto 1,2,3-triazoles was developed, which demonstrated low environmental impact through the measurement of various green metrics.
GREEN SYNTHESIS AND CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Jose Luis Osorio-Tejada, Francesco Ferlin, Luigi Vaccaro, Volker Hessel
Summary: Carbon-to-carbon (C-C) cross-coupling reaction (CCR) protocols are a major breakthrough in synthetic chemistry, widely used in medicinal chemistry and other applied sciences. This study uses life cycle assessment (LCA) to evaluate the environmental impact of CCRs, separating intrinsic and extrinsic impacts. The findings suggest the need to recycle the catalyst, carefully choose the halobenzene, and recycle the ligand along with the catalyst.