Article
Parasitology
Ana Carolina Santana Vieira, Mariana da Silva Santos, Anderson Brandao Leite, Amanda Evelyn da Silva, Luiz Henrique Agra Cavalcante-Silva, Gabrielle de Souza Augusto Pereira, Sany Delany Gomes Marques, Barbara Viviana de Oliveira Santos, Alysson Wagner Fernandes Duarte, Aline Cavalcante de Queiroz, Kristerson Reinaldo de Luna-Freire, Magna Suzana Alexandre-Moreira
Summary: Leishmaniasis is a neglected disease with limited treatment options and adverse effects. This study evaluated the antileishmanial activity of several derivatives and found that one derivative (1G) showed activity against both promastigote and amastigote forms with low toxicity to macrophages.
PARASITOLOGY RESEARCH
(2022)
Article
Chemistry, Physical
Yinuo Li, Cuiyu Bao, Zhoutong Sun, Wuyuan Zhang, Bo Yuan
Summary: The oxidation of benzylic alcohols coupled with the Morita-Baylis-Hillman (MBH) reactions in biocatalytic compatible conditions was evaluated. One-pot cascades were described and compared, including a chemoenzymatic cascade with galactose oxidase (GOase M3-5) and 1,4-Diazabicyclo [2.2.2] octane (DABCO), a concurrent dual-enzyme cascade with GOase M3-5 and a computationally designed enzyme MBHase (BH32.14), and a whole cell biotransformation with co-expression modules of the two enzymes. The cascades showed high conversions and yields, with some products having high optical purity.
Article
Chemistry, Physical
Aleksandra Buchcic-Szychowska, Anna Zawisza, Stanislaw Lesniak, Michal Rachwalski
Summary: In this study, chiral aziridine-phosphines were used as catalysts in the asymmetric Morita-Baylis-Hillman reaction. The desired chiral products were obtained in moderate to high yields and with a high enantiomeric excess. The use of enantiomeric pairs of catalysts led to the formation of products with opposite absolute configurations.
Article
Chemistry, Organic
Niannian Ni, Jiawei Chen, Siyu Ding, Dongping Cheng, Xiaonian Li, Xiaoliang Xu
Summary: The Ru-catalyzed coupling reaction of Morita-Baylis-Hillman (MBH) adducts with tertiary amines and alpha-trimethylsilyl amines under visible light showed different chemical reaction characteristics when compared to MBH adducts with ester groups as withdrawing-electron groups. The universality of substrates has been extended, allowing for the synthesis of structurally complementary acrylonitriles in satisfied yields under mild conditions and providing an opportunity to discover new meaningful bioactive compounds.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Lei Zhang, Wangzhen Bao, Yuchen Liang, Wenjing Pan, Dongyang Li, Lichun Kong, Zhi-Xiang Wang, Bo Peng
Summary: This study demonstrates the reversal of stereoselectivity in MBH-type [3,3]-rearrangement by using a new pair of rearrangement partners, leading to the synthesis of different types of alpha-aryl alpha,beta-unsaturated carbonyl derivatives. Mechanistic studies provide insights into the reaction pathway and the opposite stereoselectivities observed.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Prashant Shukla, Ambika Asati, Devkumari Patel, Manorama Singh, Vijai K. K. Rai, Ankita Rai
Summary: This study reports on the Morita Baylis-Hillman (MBH) reaction using various aldehydes with acrylonitrile and methyl acrylate as electron-deficient alkenes. A novel catalyst, EDC.HCl, is utilized in the presence of CuI to synthesize the MBH adduct. The synthetic protocol shows excellent product yield (up to 99%), ambient reaction conditions, shorter reaction time, and no side product formation.
Article
Chemistry, Organic
Naruhiro Gondo, Koki Fujimura, Ryuichi Hyakutake, Yoshihiro Ueda, Takeo Kawabata
Summary: Asymmetric regioselective vinylogous aza-Morita-Baylis-Hillman reactions were conducted using organocatalysis. The reactions between 3-vinylcyclopentenone and various aldimines, in the presence of chiral pyrrolidinopyridine catalysts, yielded 7-adducts with high regioselectivity and moderate enantioselectivity.
TETRAHEDRON LETTERS
(2023)
Review
Biochemistry & Molecular Biology
Wanyama Peter Juma, Dubekile Nyoni, Dean Brady, Moira L. Bode
Summary: The Morita-Baylis-Hillman (MBH) reaction produces highly functionalized allylic alcohols with new stereogenic centers that can be transformed into various products, some of which have medicinal potential. While some asymmetric syntheses of MBH adducts have been reported, a universally applicable method is still needed. Biocatalytic methods for synthesis and enzymatic kinetic resolution of MBH adducts have been explored, with enzymes like lipases, esterases, and nitrile-converting enzymes showing promise in achieving high selectivity in most cases.
Article
Chemistry, Physical
Ricardo Lucas Gomes Pimentel, Rodolfo B. da Silva, Mario Luiz Araujo de Almeida Vasconcellos, Claudio Gabriel Lima-Junior, Fausthon F. da Silva
Summary: This study explores the synthesis and characterization of a mixed-metal copper-manganese iminodiacetate 1D coordination polymer (Cu/Mn-IDA) and its application as a catalyst for the Morita-Baylis-Hillman reaction. The results demonstrate that under optimized conditions, the catalyst can achieve yields of up to 87% for various aldehyde substrates. Additionally, the catalyst exhibits good recyclability.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Chemistry, Organic
Jianning Liao, Jipan Dong, Jiaqing Xu, Wei Wang, Yongjun Wu, Yuxia Hou, Hongchao Guo
Summary: A phosphine-catalyzed [3 + 2] annulation reaction has been developed in this study to synthesize multifunctional isoxazoles with moderate to good yields and diastereoselectivities. The use of a spirocyclic chiral phosphine catalyst resulted in up to 89% ee.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Yi-Lin He, Miao Zhong, Zi-Long Song, Yu-Kai Shen, Lanning Zhao, Jianguo Fang
Summary: This study reports the design and synthesis of a series of Baylis-Hillman adducts, among which a typical adduct showed superior cytotoxicity against HepG2 cells. The selected typical adduct was found to selectively target TrxR in HepG2 cells, leading to the disruption of intracellular redox homeostasis. It also arrested the cell cycle and significantly restrained the metastasis of HepG2 cells. These findings suggest that the selected typical adduct, as well as other Baylis-Hillman skeleton-bearing compounds, hold promise as candidate or ancillary agents for the treatment of various cancers.
BIOORGANIC & MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Organic
Yue Wang, Manman Song, Er-Qing Li, Zheng Duan
Summary: This study presents a new palladium/phosphine cooperative catalytic system for the synthesis of bicyclo[3.1.0]hexene derivatives, highlighting the crucial roles of both Pd and phosphine in the selective intermolecular activation of Morita-Baylis-Hillman carbonates. This strategy opens up a new avenue for efficient and economical metal/Lewis base dual catalytic systems and provides valuable clues on solving the limitations of selective activation.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Sebastiano Mantovani, Angela Pintus, Alessandro Kovtun, Giulio Bertuzzi, Manuela Melucci, Marco Bandini
Summary: A metal-free synthetic approach to functionalized indenes using graphene oxide (GO) is presented in this article. The method involves intramolecular Friedel-Crafts-type allylic alkylations with Morita-Baylis-Hillman alcohols. Experimental and spectroscopic investigations were conducted to understand the reaction mechanism involving a nanostructured carbon material-based C-C bond forming reaction. The results showed that this carbocatalysis approach is a viable option for the synthesis of indenes, with a wide scope and moderate to high yield under mild reaction conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Physical
Hugo Santos, Lucas A. Zeoly, Manoel T. Rodrigues Jr, Fabio S. Fernandes, Ralph C. Gomes, Wanda P. Almeida, Fernando Coelho
Summary: Since its discovery in the late 1960s, the Morita-Baylis-Hillman (MBH) reaction has been a powerful carbon-carbon sigma-bond-forming reaction, producing small polyfunctionalized molecules. Advances in functional catalysts and reaction conditions have been made to improve the reaction rate, substrate scope, and enantioselectivity. This review provides an updated summary of the main improvements in catalytic systems for the MBH reaction over the past decade until nowadays, aiming to inspire further investigations and overcome the remaining challenges of this fascinating transformation.
Article
Chemistry, Multidisciplinary
Lucas Raposo Carvalho, Lucas Gil Venturelli, Thiago Castro Lopes, Eclair Venturini Venturini Filho, Vinicius Goncalves Fontenelle, Guilherme Ferreira de Lima, Leila Lea Yuan Visconte, Eder do Couto Tavares
Summary: Eliminating N-nitrosamines from rubber products is a challenge for the industry, and allyldithiocarbimate salts can be a viable alternative to traditional accelerators, offering better performance.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2023)
Article
Chemistry, Multidisciplinary
Feng An, Harish Jangra, Yin Wei, Min Shi, Hendrik Zipse, Armin R. Ofial
Summary: The kinetics of the reactions of tributylphosphine with allenic and olefinic Michael acceptors were studied using photometric and NMR spectroscopic methods. The relevance of retroaddition barriers in phosphine-catalysed reactions was revealed when mixtures of allenic and olefinic substrates were used.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Ben Mao, Xiao-Yu Zhang, Yin Wei, Min Shi
Summary: A concise and practical strategy for the synthesis of benzazepine derivatives has been developed through a ring-opening/cyclization cascade reaction of alpha-brominated amide-tethered alkylidenecyclopropanes in the presence of photocatalyst 4CzIPN under visible-light irradiation.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Long-Hai Li, Hao-Zhao Wei, Yin Wei, Min Shi
Summary: In this study, a strategy to overcome the limitation of the Morita-Baylis-Hillman (MBH) reaction, which is restricted to electron-deficient olefins, was achieved using visible-light induced photoredox catalysis. By employing a novel photoredox-quinuclidine dual catalysis, non-electron-deficient olefins were able to undergo the MBH reaction smoothly. Mechanistic studies, including radical probe experiments and density functional theory (DFT) calculations, were conducted to support the proposed reaction pathways.
Article
Chemistry, Organic
Zhen Liu, Yin Wei, Min Shi
Summary: This paper presents a visible-light-mediated regioselective ring-opening hydrogenolysis of donor-acceptor cyclopropanes for the synthesis of alkylated aryl ketones in moderate to excellent yields with good functional group compatibility under mild conditions. The method provides a facile and practical approach to access a variety of alkylated aryl ketones with low cost reductant. A mechanistic paradigm has been proposed based on control experiments, deuterium labeling, and H-1 NMR tracing experiments.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Jiaxin Liu, Tonggang Hao, Ling Qian, Min Shi, Yin Wei
Summary: Here, we report a method for the synthesis of a wide range of benzocyclobutanol and benzocyclobutylamine derivatives through visible-light irradiation. The reaction involves the activation of remote C(sp(3))-H bonds of olefinic compounds and proceeds via a triplet biradical atom transfer mechanism. The reaction exhibits broad substrate scope and good functional group tolerance under mild reaction conditions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Hao-Zhao Wei, Yin Wei, Min Shi
Summary: A cascade cyclization method using Weinreb amide-tethered methylenecyclopropanes and alkynes is disclosed in this paper, which extends the umpolung ring opening of methylenecyclopropanes and provides a synthetic approach for constructing polycyclic cyclopenta[b]naphthalenol framework.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Tonggang Hao, Min Shi, Yin Wei
Summary: A copper-catalyzed [5+1] cycloaddition reaction for the rapid construction of protected naphthalen-1(2H)-one derivatives has been discovered. The mechanism involves the coupling of terminal alkynes with diazo esters, followed by a 1,5-H shift process and a thermally induced pericyclic reaction.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Hao-Zhao Wei, Min Shi, Yin Wei
Summary: Diverse transformations of methylenecyclopropanes (MCPs) under visible-light irradiation have attracted significant attention from synthetic chemists. MCPs, as readily accessible strained molecules, possess sufficient reactivity to selectively generate different target products through reactions with various radical species. These transformations can be classified into three subcategories, forming ring-opened products, cyclopropane derivatives, and alkynes. This review summarizes the recent advancements in this field.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Applied
Jun-Sheng Wei, Zi-Yu Xu, Yin Wei, Min Shi
Summary: In this paper, a gold(I)-catalyzed cascade cyclization of N- or O-nucleophile tethered-vinylidenecyclopropanes (VDCPs) is reported, leading to the synthesis of pyrrole, furan, pyrrolidine, and piperidine skeletons in 30%-98% yields. The reaction pathways depend on the carbon chain length connecting the nucleophile and VDCPs, resulting in different products. By using α-amino VDCPs and α-hydroxyl VDCPs with a methylene group as the connection, intramolecular nucleophilic addition and aromatization occur, followed by ring-opening of the cyclopropane unit to produce substituted pyrroles and furans. Extending the chain length to three or four carbons enables the formation of pyrrolidines and piperidines with a cyclobutene moiety through ring expansion of the cyclopropane unit and gold carbene induced vinylogous nucleophilic addition.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Chemistry, Multidisciplinary
Jia-Hao Shen, Min Shi, Yin Wei
Summary: The combination of visible light photocatalysis and organocatalysis has been widely used in various reactions in recent years. The synergy between visible light photocatalysis and organocatalysis has led to significant progress in modern chemical synthesis. In these dual catalytic systems, photocatalysts or photosensitizers absorb visible light to activate unreactive substrates through electron or energy transfer mechanisms, while organocatalysts are used to control the reactivities of other substrates. This review primarily focuses on the recent advancements in cooperative catalysis by the combination of organocatalysis and photocatalysis in organic synthesis.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Zhe Meng, Jun Yan, Chao Ning, Min Shi, Yin Wei
Summary: This paper presents an efficient synthetic strategy for the rapid construction of multisubstituted pyrroles, furans, and thiophenes via NXS mediated desulfonylative/dehydrogenative cyclization of vinylidenecyclopropanes. The method offers advantages such as a wide substrate range, high efficiency, and synthetic usefulness of the heterocyclic products under metal-free and mild conditions. The derivatization of pyrrole products and the preparation of functional molecules demonstrate the synthetic potential of the products as platform molecules. The reaction mechanism has been investigated through control experiments and DFT calculations.
Article
Chemistry, Multidisciplinary
Jun Yan, Min Shi, Yin Wei
Summary: In this minireview, the recent asymmetric cyclization of alkynes with other functional groups such as carbonyl-alkynes, cyano-alkynes, and enynes under the catalytic system of nickel and chiral ligands is mainly summarized.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Jun-Sheng Wei, Song Yang, Yin Wei, Sima Shamsaddinimotlagh, Hossein Tavakol, Min Shi
Summary: A gold(i)-catalyzed intramolecular cyclization reaction was developed to synthesize functionalized morpholines, piperazines, and oxazepanes. The reaction proceeds via a carbene or non-carbene process and exhibits a broad substrate scope, good functional group tolerance, and mild reaction conditions. The reaction pathway can be modulated by the steric bulkiness or chain length of the substrate.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Xin-Tao Gu, Long-Hai Li, Yin Wei, Min Shi
Summary: The site selective C(sp(2))-H bond functionalization of olefins has been successfully achieved through a visible-light-induced photoredox-quinuclidine dual catalysis. This synthetic protocol offers a simple operation with readily available starting materials, providing alkenylheteroaromatic products in moderate to good yields under mild conditions. A plausible cascade catalytic reaction mechanism is proposed.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Chao Ning, Kang-Hua Rui, Yin Wei, Min Shi
Summary: In this study, the mechanism of Rh(i) complex catalyzed dimerization of ene-vinylidenecyclopropanes was elucidated through experimental and computational studies, and a key intermediate was identified.
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)
