Article
Chemistry, Organic
Zhichao Li, Lianze Zong, Xixi Hu, Xinjin Li, Feng-Gang Sun, Yunhui Dong, Zhengbao Xu, Hui Liu, Lizhi Zhang
Summary: An efficient and practical method for the phosphorylation-acylation of 2-vinyl pyridines has been developed. This protocol provides a sustainable strategy for the synthesis of novel alpha,beta-acylphosphinoyl compounds and can be easily scaled up. Mechanistic studies revealed a nucleophilic addition/oxygen transfer process.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Xinxuan Li, Hepan Wang, Tao Xu
Summary: beta-Ketophosphonates are valuable molecules in organic synthesis. A modular and direct protocol is reported for accessing alpha-substituted-beta-ketophosphonates by utilizing aldehydes and alpha-bromophosphonates via dual nickel/photoredox catalysis. Some special beta-keto frameworks were also obtained with this strategy.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Physical
Zhigang Liu, Miaolin Ke, Ke Zhang, Zexu Wang, Baijun Ye, Fener Chen
Summary: A first simple palladium catalyzed allylation of vinylethylene carbonates with beta-ketophosphonates has been developed, providing access to (Z)-tri- and tetrasubstituted homoallylic phosphonates with exclusive regioselectivity, chemoselectivity and (Z)-stereoselectivity. The reaction tolerates a wide substrate scope and works well on the gram scale.
Article
Chemistry, Organic
Yong-Wang Huo, Lingyun Yao, Xinxin Qi, Xiao-Feng Wu
Summary: A nickel-catalyzed reductive aminocarbonylation reaction has been developed for the synthesis of alpha,beta-unsaturated amides, using vinyl triflates and nitroarenes as starting materials. The method shows excellent functional group tolerance and can achieve high yields of the desired products. This study also demonstrates a potential late-stage modification strategy for natural products using the reductive aminocarbonylation approach.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Roxana Postolache, Juana M. Perez, Marta Castineira Reis, Luo Ge, Esther G. Sinnema, Syuzanna R. Harutyunyan
Summary: In this study, catalytic asymmetric hydrophosphination of α,β-unsaturated carbonyl derivatives using a chiral Mn(I) complex as a catalyst is reported. Various phosphine-containing chiral products can be obtained through H-P bond activation via hydrophosphination of different ketone, ester, and carboxamide-based Michael acceptors.
Article
Chemistry, Multidisciplinary
Swetha Jos, Christine Tan, Pierre Thilmany, Alaa Saadane, Carla Slebodnick, Gwilherm Evano, Webster L. Santos
Summary: We have reported a tri-n-butyl phosphine catalyzed hydroboration reaction of ynamides, which provides regio- and stereo-selective formation of (Z)-beta-borylenamides in good yields. Surprisingly, a formal cis addition to the triple bond was observed, and this finding was confirmed by NMR and X-ray crystallography. P-31 NMR studies suggest that a zwitterionic vinylphosphonium intermediate plays a key role in the reaction mechanism. Furthermore, the resulting products were successfully transformed into beta-CF3 enamides via stereoretentive trifluoromethylation.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Yuyang Bai, Liping Cao, Siyuan Li, Guang'an Zhang, Yingguo Liu, Fengqian Zhao, Junliang Wu
Summary: A photoredox/Lewis acid cooperative catalytic system has been developed for the construction of C-vinyl-C-Rf bonds through the dehydrative difluoroalkylation of benzyl alcohols. Various allylic gem-difluorides were obtained with moderate yields and good to excellent E/Z selectivity. Control experiments were conducted and a possible mechanism for this process was proposed.
Article
Chemistry, Organic
Litao Zhou, Ruoxin Huang, Shaohang Lu, Bingxin Liu, Mingchun Gao, Bin Xu
Summary: A regio- and stereoselective direct nitration of vinylcyclopropanes with Cu(NO3)2 and KI is described, which efficiently affords nitroalkenes while preserving the cyclopropane skeleton. The method can be extended to other vinylcycles and biomolecule derivatives with a wide substrate scope, good functionality tolerance, and efficient synthesis modularity. Further transformations demonstrate the versatility of the obtained products as building blocks in organic synthesis. The proposed ionic pathway explains the intact small ring and the effect of KI during the reaction.
Article
Chemistry, Multidisciplinary
Zhi-Peng Bao, Youcan Zhang, Xiao-Feng Wu
Summary: The introduction of fluorine atoms into organic molecules is an attractive topic. This work developed an interesting palladium-catalyzed reaction to transform aryl olefins into difluoropentanedioate compounds with good functional-group tolerance and high regioselectivity. Ethyl bromodifluoroacetate acts as both a difluoroalkyl precursor and a nucleophile in this reaction. Additionally, successful scale-up reactions and further transformations of the obtained product were demonstrated.
Article
Chemistry, Multidisciplinary
Jianxiao Li, Zidong Lin, Dan He, Wanqing Wu, Huanfeng Jiang
Summary: This study presents a novel and viable palladium-catalyzed sequential cyclization/functionalization of alkynone O-methyloximes with unactivated vinyl ethers under aerobic conditions. The structure of the products can be successfully controlled by varying the nature of the substituents of the vinyl ethers. This method offers a convenient and straightforward synthetic protocol for preparing structurally diverse compounds with promising applications in synthetic and pharmaceutical chemistry, even on a gram scale.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Meng Zhao, Ying Wang, Zi-Lu Wang, Jian-Lin Xu, Kai-Yang Dai, Yun-He Xu
Summary: In this study, copper-catalyzed diverse silylative carbocyclization reactions were reported, leading to the discovery of three new types of domino reactions for the transformation of silaboronate with high efficiency and selectivity.
Article
Chemistry, Organic
Yunhe Lv, Wanru Han, Weiya Pu, Jinhui Xie, Axue Wang, Mengyue Zhang, Jin Wang, Junrong Lai
Summary: A novel and practical copper-catalyzed reaction for 1,4-sulfonylcyanation of 1,3-enynes under mild conditions is described. The reaction provides efficient access to a variety of 5-sulfonylpenta-2,3-dienenitrile derivatives with excellent functional group tolerance and selectivity.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Jian-Xing Xu, Zhi-Peng Bao, Xiao-Feng Wu
Summary: The transformation of carbon monoxide and ethylene into high value-added chemicals, particularly multifunctionalized compounds, is economically significant. A palladium-catalyzed thiocarbonylative 1,2-difunctionalization of ethylene was developed, resulting in successful conversion of organic disulfides into beta-thiopropionate thioesters with good yields.
Article
Chemistry, Multidisciplinary
Nilanjana Mukherjee, Tanmay Chatterjee
Summary: This study discloses a metal-free, iodine-catalyzed oxidative C-H sulfenylation and selenation of alkenes in water, which provides a cost-effective, highly atom-economical, and sustainable synthesis method for valuable vinyl sulfides and selenides, including some aggregation-induced-emission (AIE) active molecules. The method shows several advantages, such as the use of inexpensive reagents, water as the reaction medium, high reaction efficiency, and excellent green chemistry metrics.
Article
Chemistry, Organic
Zhi-Xin Chang, Fei-Yuan Gong, Xiaodan Wang, Tongbo Zhang, Junfen Han, Hong-Shuang Li
Summary: This study reveals the mechanistic pathway of the formal hydroacylation reactions of vinyl epoxides with chelating aldehydes enabled by rhodium catalysis, highlighting the importance of the presence of a 2-vinyl group for the success of the regioselective reaction.
Article
Chemistry, Physical
Yanina Moglie, Eduardo Buxaderas, Agustina Mancini, Francisco Alonso, Gabriel Radivoy
Article
Chemistry, Physical
Grigoriy N. Bondarenko, Ekaterina G. Dvurechenskaya, Olga G. Ganina, Francisco Alonso, Irina P. Beletskaya
APPLIED CATALYSIS B-ENVIRONMENTAL
(2019)
Article
Biochemistry & Molecular Biology
Fabian Santana-Romo, Carlos F. Lagos, Yorley Duarte, Francisco Castillo, Yanina Moglie, Miguel A. Maestro, Nitin Charbe, Flavia C. Zacconi
Article
Nanoscience & Nanotechnology
Alexander V. Sirotkin, Monika Radosova, Adam Tarko, Iris Martin-Garcia, Francisco Alonso
Article
Chemistry, Multidisciplinary
Alexander Sirotkin, Monika Radosova, Adam Tarko, Zuzana Fabova, Iris Martin-Garcia, Francisco Alonso
Article
Chemistry, Multidisciplinary
Luciano A. Benedini, Yanina Moglie, Juan M. Ruso, Sofia Nardi, Paula Messina
Summary: This study evaluates the chemical grafting of phosphorous amide and alpha-amino phosphonate molecular fragments on previously created biomimetic hydroxyapatite nanoparticles, providing a new application for the liquid crystal properties of biological molecular networks. The results demonstrate that under specific synthetic conditions, it is possible to obtain nanoparticles that act as mesogenic agents and self-assemble under pH stimulation.
CRYSTAL GROWTH & DESIGN
(2021)
Article
Chemistry, Multidisciplinary
Yanina Moglie, Evangelina Mascaro, Flavia Zacconi, Gabriel Radivoy
Summary: Copper nanoparticles supported on ZnO exhibit high activity and selectivity in the N-arylation of cyclic and acyclic amides, with mild reaction conditions and the ability to be reused multiple times without significant loss of activity. The methodology can also be successfully scaled up to gram scale without diminishing catalytic activity.
Review
Chemistry, Multidisciplinary
Diego F. Rodriguez, Yanina Moglie, Cesar A. Ramirez-Sarmiento, Sachin Kumar Singh, Kamal Dua, Flavia C. Zacconi
Summary: The fields of click chemistry and biocatalysis have grown rapidly, leading to significant interactions between these two fields. Bio-click chemistry, which combines biocatalytic enzyme activity with click reactions, offers a green and sustainable approach for the synthesis of high-value molecules, particularly chiral molecules with applications in medicinal chemistry and sustainable syntheses.
Article
Pharmacology & Pharmacy
Diego F. Rodriguez, Francisca Duran-Osorio, Yorley Duarte, Pedro Olivares, Yanina Moglie, Kamal Dua, Flavia C. Zacconi
Summary: Implementation of green chemistry has shown promising results in waste reduction in the pharmaceutical industry. However, sustainable development of pharmaceutically active compounds and ingredients remains challenging. In this study, a green synthesis method was used to produce pharmaceutically active peptide triazoles as potent factor Xa inhibitors, important drug targets for cardiovascular diseases. The synthesis involved cycloaddition reactions with high atom economy, microwave-assisted organic synthesis for energy efficiency, and copper nanoparticle catalysis with Earth-abundant metals. The synthesized molecules demonstrated FXa inhibition with low IC50 values and no cytotoxicity in HEK293 and HeLa cells, highlighting the environmental potential and chemical implications of the applied methodologies for new molecule development.
Article
Biochemistry & Molecular Biology
Jose J. Delgado-Marin, Iris Martin-Garcia, David Villalgordo-Hernandez, Francisco Alonso, Enrique Ramos-Fernandez, Javier Narciso
Summary: One potential way to utilize CO2 is to react it with organic epoxides to produce cyclic carbonates. However, no efficient and selective heterogeneous catalyst has been discovered yet. In this study, cobalt and zinc-based zeolitic imidazole frameworks (ZIFs) were explored as catalysts for this reaction. Modified ZIF-8 and ZIF-67 catalysts were prepared and showed excellent catalytic performance in the cycloaddition of CO2 with epichlorohydrin. Notably, these reactions occurred under mild conditions without the need for co-catalysts.
Article
Biochemistry & Molecular Biology
Mahzad Yaghmaei, Martin Villanueva, Iris Martin-Garcia, Francisco Alonso, Xiaocong Zhang, Neeraj Joshi, Anabel E. Lanterna, Juan C. Scaiano
Summary: Selective semi-oxidation of tetrahydroisoquinoline (THIQ) can be achieved through singlet oxygen photooxidation process, leading to a valuable dihydroisoquinoline (DHIQ) derivative. Photosensitisers can activate the reaction even under heterogeneous conditions and can be combined with semiconductor catalysts to improve reaction efficiency and catalyst separability and reusability.
PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES
(2022)
Article
Chemistry, Physical
Iris Martin-Garcia, Gloria Diaz-Reyes, George Sloan, Yanina Moglie, Francisco Alonso
Summary: Sulfur has been found to be an effective stabilizing agent for copper nanoparticles, allowing for their application in organic medium catalytic reactions; The Cu(2)ONPs/S-8 system shows promising results in solvent-free aerobic oxidation of primary amines to imines, with potential for various applications; A proposed reaction mechanism based on experimental evidence provides insight into key intermediates, suggesting new research avenues in nanocatalysis.
JOURNAL OF MATERIALS CHEMISTRY A
(2021)
Review
Chemistry, Organic
Irene Bosque, Rafael Chinchilla, Jose C. Gonzalez-Gomez, David Guijarro, Francisco Alonso
ORGANIC CHEMISTRY FRONTIERS
(2020)
Review
Chemistry, Multidisciplinary
Francisco Alonso, Irene Bosque, Rafael Chinchilla, Jose Carlos Gonzalez-Gomez, David Guijarro
CURRENT GREEN CHEMISTRY
(2019)
