Article
Chemistry, Organic
Suguru Murakami, Ryosuke Matsubara, Masahiko Hayashi
Summary: In this study, the reaction between alkynes and bis(pinacolato)diboron in the presence of [Cp*RuCl2](n) was successfully applied to synthesize (Z)-1,2-diboryl alkenes. The addition of NaOC6H4(4-tBu) and methanol in proper amounts was crucial for achieving high product yield. The obtained 1,2-diboryl alkenes served as precursors for tetrasubstituted alkenes.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Sebastian Puschel, Sven Stortte, Johanna Topphoff, Andreas J. Vorholt, Walter Leitner
Summary: CO2-neutral fuels produced through Fischer-Tropsch synthesis using bio-syngas offer a promising pathway for sustainable mobility. Recent advancements in FT catalyst research have enabled the conversion of olefin-enriched products into alcohol-enriched fuels with favorable combustion behavior. A study on the hydroformylation-hydrogenation sequence of FT-olefin-paraffin mixtures demonstrated effective catalyst recycling and achieved high turnover numbers for the conversion of olefins to alcohols in continuously operated processes.
Article
Chemistry, Organic
Lilla G. Gombos, Leo Werner, Dieter Schollmeyer, Carlos A. Martinez-Huitle, Siegfried R. Waldvogel
Summary: A simple electrochemical protocol has been developed for the selective alkene dibromination of naturally derived olefins. This protocol avoids the use of hazardous Br-2 or its analogues by utilizing readily available, inexpensive, and harmless sodium bromide as a reagent and supporting electrolyte, along with sustainable carbon-based electrodes. The protocol achieves high yields of the desired products and has demonstrated scalability.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(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.
Review
Chemistry, Multidisciplinary
Leandro Duarte de Almeida, Hongli Wang, Kathrin Junge, Xinjiang Cui, Matthias Beller
Summary: This minireview discusses the use of homogeneous noble metal catalysts and earth-abundant transition metals/heterogeneous catalysts in hydrosilylation reactions, highlighting the growing interest in more sustainable and economic catalysts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
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, 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, 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, Organic
Qian Tu, Zheyuan Wang, Zhongchao Zhang, Jun Huang, Zhen Yang
Summary: The structurally intriguing tetracyclic core of complex harziane diterpenoid was successfully constructed in 14 steps from commercially available compound. Key methods used include Mn/Cu-mediated oxidative 1,3-dicarbonyl radical cascade cyclization reaction and Au-catalyzed diastereoselective formal [2 + 2] cycloaddition.
Article
Chemistry, Organic
Jinfeng Huang, Yimin Jia, Xiangyu Li, Jianli Duan, Zhong-Xing Jiang, Zhigang Yang
Summary: A highly regioselective copper-catalyzed reaction has been developed for the first time to access tetrasubstituted allene derivatives containing halogen and CF3 groups with good to excellent yields. This practical and convenient method is compatible with a wide range of functional groups and has shown promising applications in the gram-scale preparation and late-stage functionalization of biologically active molecules.
Article
Chemistry, Organic
Hong-Chao Liu, Xiao-Ping Gong, Yu-Zhao Wang, Zhi-Jie Niu, Heng Yue, Xue-Yuan Liu, Yong-Min Liang
Summary: A novel Ru-catalyzed regioselective alkylarylation of vinylarenes with alkyl halides and arenes via meta-C(sp(2))-H bond functionalization has been reported. This reaction shows excellent substrate tolerance and regioselectivity, as well as redox-neutral conditions.
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
Wen-Jun Yue, Craig S. Day, Adrian J. Brenes Rucinski, Ruben Martin
Summary: We present a modular catalytic technique that simplifies the preparation of gem-difluoroalkanes from unactivated sp3 precursors. This method exhibits simplicity, generality, and site selectivity, allowing for the functionalization of advanced intermediates and olefin feedstocks. Our strategy involves a cooperative interplay of halogen- and hydrogen-atom transfer, providing a new entry point to difluorinated alkyl bioisosteres of interest in drug discovery.
Article
Chemistry, Organic
Huaxin Yang, Yang Zhou, Zhihan Zhang, Jialin Wen, Xumu Zhang
Summary: We report a convenient method for converting olefins to organic iodides and amines using a specific catalyst, molecular hydrogen, and an electrophilic iodine reagent. High yields and regioselectivities were achieved under mild conditions, and C-N products were obtained through specific workup steps. Control experiments and DFT calculations were conducted to exclude potential reaction pathways.
Article
Chemistry, Applied
Nora Jannsen, Cornelia Pribbenow, Carmen Selle, Hans-Joachim Drexler, Marc-Andre Mueller, Jonathan A. Medlock, Werner Bonrath, Detlef Heller
Summary: An efficient and highly selective semi-hydrogenation of terminal alkynes to alkenes has been achieved using neutral dimeric rhodium(I) complexes. The results show excellent selectivity and no deactivation or reduction in selectivity, indicating the potential industrial application of homogeneous rhodium complexes in the semi-hydrogenation of terminal alkynes.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Physical
Gabriel M. Vieira, Artur V. Granato, Elena V. Gusevskaya, Eduardo N. dos Santos, Pierre H. Dixneuf, Cedric Fischmeister, Christian Bruneau
APPLIED CATALYSIS A-GENERAL
(2020)
Article
Chemistry, Applied
Niklas Zwettler, Antoine Dupe, Sumea Klokic, Angela Milinkovic, Dado Rodic, Simon Walg, Dmytro Neshchadin, Ferdinand Belaj, Nadia C. Moesch-Zanetti
ADVANCED SYNTHESIS & CATALYSIS
(2020)
Review
Chemistry, Physical
Hallouma Bilel, Naceur Hamdi, Cedric Fischmeister, Christian Bruneau
Article
Chemistry, Organic
Harikrishnan Jayaprakash, Liwei Guo, Shengdong Wang, Christian Bruneau, Cedric Fischmeister
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Review
Chemistry, Inorganic & Nuclear
Rafael Gramage-Doria, Christian Bruneau
Summary: Ruthenium complexes are widely recognized as excellent pre-catalysts for challenging C-H bond functionalization reactions, and their combination with other types of chemical reactions can reduce purification and isolation steps, increasing reaction sustainability. Research in this field focuses on the compatibility of different reaction sequences, with a particular emphasis on the compatibility of ruthenium-catalyzed C-H bond functionalization with organic transformations, metal-mediated reactions, and transition metal catalysis.
COORDINATION CHEMISTRY REVIEWS
(2021)
Editorial Material
Chemistry, Inorganic & Nuclear
Jean-Francois Soule, Christian Bruneau, Christophe Darcel
Review
Chemistry, Multidisciplinary
Salekh M. Masoud, Dania V. Vorobyeva, Dmitry A. Petropavlovskikh, Christian Bruneau, Sergey N. Osipov
Summary: This review summarizes literature data on methods for introducing fluorine atoms and fluoralkyl groups into different ligands to construct metathesis-active ruthenium carbene complexes, analyzing their influence on catalytic activity. The choice of fluorinated substituents in NHC ligands aims to increase ruthenium atom electrophilicity and enhance complex activity; introducing polyfluoroalkyl groups can help solve the issue of catalyst recovery.
RUSSIAN CHEMICAL REVIEWS
(2021)
Article
Chemistry, Physical
Luciana Sarmento Fernandes, Dalmo Mandelli, Wagner A. Carvalho, Elsa Caytan, Cedric Fischmeister, Christian Bruneau
Summary: The direct functionalization of sterically demanding alpha,alpha-disubstituted double bonds in beta-pinene, (-)-limonene and (-)-limonene terpenoids has been achieved through cross metathesis with internal olefins. This clean transformation provides a new method for accessing functionalized bulky cyclic terpenes, where the terminal double bond generates a trisubstituted olefin.
APPLIED CATALYSIS A-GENERAL
(2021)
Article
Chemistry, Multidisciplinary
Angela Milinkovic, Antoine Dupe, Ferdinand Belaj, Nadia C. Moesch-Zanetti
Summary: Molybdenum(VI) bis(imido) complexes with frustrated Lewis pair characteristics can heterolytically split H-H, Si-H, and O-H bonds. These complexes can be used as catalysts for the hydrosilylation reaction. Mechanistic elucidation revealed the insertion of aldehydes into the B-H bond of the molybdenum complexes, highlighting the weakly coordinating cation behavior of molybdenum.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Biochemistry & Molecular Biology
Thalita S. Galhardo, Anderson K. Ueno, Thais A. Costa-Silva, Andre G. Tempone, Wagner A. Carvalho, Cedric Fischmeister, Christian Bruneau, Dalmo Mandelli, Joao Henrique G. Lago
Summary: In this study, compounds isolated from N. leucantha were used as starting material to synthesize two new derivatives, which showed activity against trypanosome and no toxicity to mammalian cells. Mechanism study revealed that the derivatives caused depolarization of the parasite's plasma membrane and collapse of mitochondrial membrane potential. Therefore, this compound could be a potential candidate for future drug design in the treatment of Chagas disease.
CHEMICO-BIOLOGICAL INTERACTIONS
(2022)
Article
Chemistry, Physical
Thalita S. Galhardo, Anderson K. Ueno, Wagner A. Carvalho, Thais A. Costa-Silva, Marina M. Goncalves, Mariana B. Abiuzi, Andre G. Tempone, Joao Henrique G. Lago, Dalmo Mandelli, Cedric Fischmeister, Christian Bruneau
Summary: Ruthenium-catalyzed cross metathesis of biseugenol with electron-deficient olefins resulted in the synthesis of derivatives 3a-3e in good yields and excellent conversion rates. The antitrypanosomal activity of these compounds against Trypanosoma cruzi was evaluated, and compounds 3b and 3d showed similar IC50 values to biseugenol, but with reduced toxicities and similar selectivity indexes to the standard drug benznidazol.
Article
Chemistry, Physical
Naba Abuhafez, Herve Ruffin, Raghu Kamaraj, Christian Bruneau, Rafael Gramage-Doria
Summary: A new method for the synthesis of 1,3-diene building blocks using ruthenium-catalyzed oxidative homo- and cross-coupling is reported, which mainly produces the E,E isomer. This methodology also allows for the synthesis of adipic acid ester derivatives in a one-pot fashion after in situ ruthenium-catalyzed hydrogenation.
CATALYSIS SCIENCE & TECHNOLOGY
(2021)
Article
Chemistry, Physical
Julien Hervochon, Vincent Dorcet, Kathrin Junge, Matthias Beller, Cedric Fischmeister
CATALYSIS SCIENCE & TECHNOLOGY
(2020)