Article
Chemistry, Multidisciplinary
Jianfeng Jiang, Xia Wang, Shengping Liu, Sichen Zhang, Binmiao Yang, Yu Zhao, Shenci Lu
Summary: We report an unprecedented gold and oxidative NHC relay catalysis for highly enantioselective cascade annulation between readily available alpha-amino-ynones with enals. This method utilizes in situ-generated pyrrolin-4-ones as a novel and versatile synthon, reacting with alpha,beta-unsaturated acylazolium intermediates generated from enals by oxidative NHC catalysis to produce pyrrole-fused lactones in high yield and excellent enantioselectivity. The utility of the lactone products is demonstrated by their facile conversion to densely functionalized pyrroles and pyrrolin-4-ones with high yields and excellent stereopurity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Jun-Jie Tian, Wei Sun, Rui-Rui Li, Gui-Xiu Tian, Xiao-Chen Wang
Summary: A borane/gold(I) co-catalytic system was designed and applied in C-H functionalization reactions and cycloaddition reactions between tertiary amines and alpha-alkynylenones, efficiently introducing a furan ring into the amine molecule.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Dominik Birnthaler, Rok Narobe, Eliseo Lopez-Berguno, Christoph Haag, Burkhard Koenig
Summary: Ligand-to-metal charge transfer (LMCT) photo-catalysis enables the activation and utilization of halides and other heteroatoms in metal complexes. The application of bismuth LMCT in organic radical coupling reactions has been expanded, generating chlorine and carboxyl radicals in net-oxidative and redox-neutral photochemical reactions. The study reveals BiCl4- and BiCl52- as the catalytically active bismuth species under 385 nm irradiation, providing insight into the reactivity of the highly reactive bismuth(II) catalyst fragment through cyclic voltammetry and UV-vis studies.
Review
Chemistry, Multidisciplinary
Sergio Gonzalez-Granda, Jesus Albarran-Velo, Ivan Lavandera, Vicente Gotor-Fernandez
Summary: The combination of metal-, photo-, enzyme-, and/or organocatalysis is a versatile approach in synthetic chemistry, particularly for the creation of chiral centers. This review focuses on the recent developments in the simultaneous use of enzymes and transition metal catalysts, as well as the integration of multiple bioprocesses and metal-catalyzed transformations in linear cascades. Challenges such as catalyst compatibility, reaction media, and cross-reactivities are addressed by strategies such as catalyst coimmobilization, compartmentalization, and flow chemistry. The review also highlights the application of bionanohybrid materials, where enzymes and metals are coimmobilized on suitable supports.
Article
Chemistry, Applied
Miguel A. Munoz-Torres, Fernando Martinez-Lara, Marta Solas, Samuel Suarez-Pantiga, Roberto Sanz
Summary: The combination of organolithium chemistry with gold catalysis offers a new synthetic strategy for accessing polysubstituted indoles and carbazoles. This method utilizes ketopyrroles as starting materials and involves a series of reactions to selectively synthesize the desired products.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Tatiana Suarez-Rodriguez, Angel L. Suarez-Sobrino, Alfredo Ballesteros
Summary: Gold(I)-catalyzed higher-order [8+2] cycloadditions of 8-aryl-8-azaheptafulvenes with allenamides and ynamides were studied, resulting in the formation of 1,8-dihydrocycloheptapyrroles and 2-amido-1,4-dihydrocycloheptapyrroles, respectively. The reactions proceeded with good yields and various substituents, suggesting a nucleophilic attack mechanism involving the gold-activated electron-rich moieties of the allenamide and ynamide.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Applied
Fernando Martinez-Lara, Anisley Suarez, Noelia Velasco, Samuel Suarez-Pantiga, Roberto Sanz
Summary: The gold-catalyzed transformation of propargylic glycols with thiols results in the formation of alpha-indol-3-yl alpha-((Z)-2-thioalkenyl) ketones through a complex but selective reaction mechanism. This sequence involves regioselective thiolation of indolyl diols followed by the attack of sulfur on the activated alkyne, rather than the indole. The final compounds are obtained in high yields from simple starting materials such as indolyl acyloins, ethynyl magnesium bromide, and thiols.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Yunxiao Zhang, Yunhong Niu, Youyuan Guo, Jiaxin Wang, Yizhi Zhang, Shanshan Liu, Xiao Shen
Summary: In this study, photocatalyzed cascade reactions between readily available cyclopropanols and alpha-trifluoromethyl-substituted olefins were reported for the synthesis of fused gem-difluorooxetanes. Two rings and three bonds were efficiently constructed in one reaction. The reaction demonstrated broad substrate scope and the downstream transformations of the products highlighted the synthetic potential. Mechanistic study supported the presence of cascade photoredox catalysis and energy transfer catalysis/direct photo-excitation processes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
T. Ghosh, S. Bhakta
Summary: This review summarizes recent developments (from 2006 to 2022) in the synthesis of important and efficient carbo- and heterocycles using gold-catalyzed cascade protocols. The methodologies discussed in this paper involve controlling selectivity, cost-effectiveness, and ease of product formation through the ligand, counter anion, catalyst, substrate, and reaction conditions. Gold-catalyzed cascade reactions encompass different strategies, including cyclization, hydroarylation, intermolecular and intramolecular cascade reactions, and more. This type of reaction is valuable for the synthesis of spiro, fused, bridged carbo- and heterocycles.
Article
Chemistry, Multidisciplinary
Morgane de Robichon, Thilo Kratz, Frederike Beyer, Julian Zuber, Christian Merten, Thorsten Bach
Summary: Substituted bicyclo[1.1.0]butanes add enantioselectively to 2(1H)-quinolones upon irradiation, leading to the formation of products with a chiral bicyclo[2.1.1]hexane skeleton. A two-point hydrogen bond between the quinolone and the template is responsible for stereocontrol in the photocycloaddition reaction. The chiral template can be recovered and reused, and sensitization is a suitable tool for performing the reaction with visible light.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Review
Chemistry, Organic
Pascal Matton, Steve Huvelle, Mansour Haddad, Phannarath Phansavath, Virginie Ratovelomanana-Vidal
Summary: Metal-catalyzed [2+2+2] cycloaddition is a powerful method for the rapid construction of functionalized 6-membered carbo- and heterocycles with high functional group tolerance. The reaction is usually regio- and chemoselective, but challenges remain for intermolecular reactions involving multiple alkynes.
SYNTHESIS-STUTTGART
(2021)
Review
Acoustics
Ingrid V. Machado, Jhonathan R. N. dos Santos, Marcelo A. P. Januario, Arlene G. Correa
Summary: By utilizing ultrasound-assisted multicomponent reactions under heterogeneous catalysis, it is possible to efficiently synthesize biologically active organic compounds with reduced costs and energy consumption.
ULTRASONICS SONOCHEMISTRY
(2021)
Article
Chemistry, Organic
Antonia Rinaldi, Vittoria Lange, Dina Scarpi, Ernesto G. Occhiato
Summary: In this study, the synthesis of (+/-)-epi-jungianol was successfully achieved through a gold(I)-catalyzed propargyl Claisen rearrangement/hydroarylation cascade reaction of suitably substituted propargyl vinyl ethers. Two different routes were compared, with the one involving substrates with less substitution on the vinyl moiety providing a higher overall yield despite requiring two additional steps. Additionally, a method for preparing acid-sensitive propargyl vinyl ethers with an alpha-alkyl-substituted vinyl moiety and their reactivity under gold catalysis was reported.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Cristian Cavedon, Sebastian Gisbertz, Susanne Reischauer, Sarah Vogl, Eric Sperlich, John H. Burke, Rachel F. Wallick, Stefanie Schrottke, Wei-Hsin Hsu, Lucia Anghileri, Yannik Pfeifer, Noah Richter, Christian Teutloff, Henrike Mueller-Werkmeister, Dario Cambie, Peter H. Seeberger, Josh Vura-Weis, Renske M. van der Veen, Arne Thomas, Bartholomaus Pieber
Summary: We demonstrate visible-light-mediated carbon-heteroatom cross-coupling reactions using a photoactive Ni(II) precatalyst. The activation of this precatalyst involves an initial intraligand charge transfer event triggered by visible light irradiation. Additionally, a porous, recyclable organic polymer for heterogeneous nickel catalysis of cross-coupling reactions is obtained through ligand polymerization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
David M. Upp, Rui Huang, Ying Li, Max J. Bultman, Benoit Roux, Jared C. Lewis
Summary: Artificial metalloenzymes (ArMs) were engineered to catalyze diazo cross-coupling resulting in high enantioselectivity alkene reduction to alkane in a one-pot cascade reaction. Directed evolution improved reaction yields and selectivities for various substrates. Molecular dynamics simulations of ArM variants were used to understand the structural role of the cofactor on ArM conformational dynamics, highlighting the ability of ArMs to control both catalyst stereoselectivity and chemoselectivity in complex media.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Alicia Galvan, Raquel Fontaneda, Francisco J. Fananas, Felix Rodriguez
ADVANCED SYNTHESIS & CATALYSIS
(2016)
Article
Chemistry, Organic
Patricia Garcia-Garcia, Ana M. Sanjuan, Muhammad A. Rashid, Alberto Martinez-Cuezva, Manuel A. Fernandez-Rodriguez, Felix Rodriguez, Roberto Sanz
JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Organic
Patricia Fernandez, Pedro Alonso, Francisco J. Fananas, Felix Rodriguez
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Pedro Alonso, Raquel Fontaneda, Pilar Pardo, Francisco J. Fananas, Felix Rodriguez
Article
Chemistry, Multidisciplinary
Raquel Fontaneda, Francisco J. Fananas, Felix Rodriguez
CHEMICAL COMMUNICATIONS
(2018)
Article
Chemistry, Organic
Patricia Fernandez, Carlos Valdes, Francisco J. Fananas, Felix Rodriguez
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
Lara Cala, Ivan Rivilla, Fernando P. Cossio, Francisco J. Fananas, Felix Rodriguez
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Chemistry, Organic
Lara Cala, Ruben Rubio-Presa, Olaya Garcia-Pedrero, Francisco J. Fananas, Felix Rodriguez
Article
Chemistry, Organic
Ruben Rubio-Presa, Olaya Garcia-Pedrero, Pablo Lopez-Matanza, Pablo Barrio, Felix Rodriguez
Summary: This method for vicinal dihalogenation of alkenes is simple, efficient, and eco-friendly, utilizing environmentally benign solvents and avoiding purification steps. Pure products are typically obtained through a simple aqueous workup.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Olaya Garcia-Pedrero, Felix Rodriguez
Summary: Cyclization reactions using cationic intermediates with alkynes as terminating groups offer wide synthetic possibilities, serving as precursors for different functionalities. This type of process shows potential, particularly in the biomimetic synthesis of natural products.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Cintia Virumbrales, Mahmoud A. E. A. A. A. El-Remaily, Samuel Suarez-Pantiga, Manuel A. Fernandez-Rodriguez, Felix Rodriguez, Roberto Sanz
Summary: This study describes a gold(I)-catalyzed cascade reaction for the stereoselective synthesis of sulfur- or selenium-containing indeno[1,2-b]chromene derivatives, involving a double cyclization process to form polycyclic structures by a proposed key gold-cyclopropyl carbene intermediate.
Article
Chemistry, Multidisciplinary
Lara Cala, Olaya Garcia-Pedrero, Ruben Rubio-Presa, Francisco J. Fananas, Felix Rodriguez
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Lara Cala, Pedro Villar, Angel R. de Lera, Francisco J. Fananas, Rosana Alvarez, Felix Rodriguez
Article
Chemistry, Multidisciplinary
Pedro Alonso, Pilar Pardo, Raquel Fontaneda, Francisco J. Fananas, Felix Rodriguez
CHEMISTRY-A EUROPEAN JOURNAL
(2017)
Article
Chemistry, Multidisciplinary
Patricia Fernandez, Francisco J. fananas, Felix Rodriguez
CHEMISTRY-A EUROPEAN JOURNAL
(2017)