Article
Chemistry, Multidisciplinary
Vladimir Akhmetov, Mikhail Feofanov, Dmitry Sharapa, Konstantin Amsharov
Summary: The ability to induce powerful atom-economic transformation of alkynes is a key feature of carbophilic pi-Lewis acids, such as gold- and platinum-based catalysts. This study demonstrates that thermally activated gamma-Al2O3 can activate enynes, diynes, and arene-ynes in a manner enabling reactions typically assigned to softest pi-Lewis acids, with a qualitative explanation based on the Dewar-Chatt-Duncanson model.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Antonio Arcadi, Giancarlo Fabrizi, Andrea Fochetti, Roberta Franzini, Francesca Ghirga, Antonella Goggiamani, Antonia Iazzetti, Federico Marrone, Andrea Serraiocco
Summary: A regioselective method using a gold (I) catalyst has been developed for the construction of polycyclic chromene cores, with good to excellent yields and a broad range of substrates, providing an efficient tool for synthesizing pyranochromene derivatives. Additionally, the regiochemical control of annulation of unsymmetrically substituted propargylic ethers has been studied, focusing on the electronic/steric effects of gold complexes and the electronic effects of aromatic ring substituents.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Antonio Arcadi, Giancarlo Fabrizi, Andrea Fochetti, Roberta Franzini, Francesca Ghirga, Antonella Goggiamani, Antonia Iazzetti, Federico Marrone, Andrea Serraiocco
Summary: A regioselective gold (I)-catalyzed approach has been developed for constructing polycyclic chromene cores with good to excellent yields under mild conditions, providing an efficient tool for synthesizing pyranochromene derivatives. Investigation into the regiochemical control of the annulation of unsymmetrically substituted propargylic ethers has focused on the electronic/steric effects of the ligands of gold complexes and the electronic effects of groups on the aromatic rings.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Karim Muratov, Fabien Gagosz
Summary: In this research, a new class of structurally simple and easily accessible bulky tri-(ortho-biaryl)phosphine ligands and their gold(I) complexes were synthesized. Their confined nature was demonstrated through X-ray diffraction analysis and comparative evaluation. Despite their notable steric congestion, these complexes exhibited remarkable catalytic activities and unusual selectivities, making them unique in the field of synthetic homogeneous gold catalysis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Marta Solas, Samuel Suarez-Pantiga, Roberto Sanz
Summary: This study describes the asymmetric synthesis of cyclopentachromenones from gold-catalyzed reaction of readily available skipped alkenynones. The cascade reaction involves an initial anti-Michael hydroarylation and a subsequent Nazarov cyclization. Excellent enantiomeric ratios and chemical yields are achieved under mild reaction conditions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Biochemistry & Molecular Biology
Antonio Arcadi, Andrea Calcaterra, Giancarlo Fabrizi, Andrea Fochetti, Antonella Goggiamani, Antonia Iazzetti, Federico Marrone, Vincenzo Marsicano, Giulia Mazzoccanti, Andrea Serraiocco
Summary: An alternative synthetic route to functionalized 1,2-dihydroquinolines using Au(I) catalysis has been reported. This method is based on the use of N-ethoxycarbonyl protected-N-propargylanilines as building blocks, resulting in good yields. The regiodivergent cyclization at the ortho-/para position is achieved through catalyst fine tuning when N-ethoxycarbonyl-N-propargyl-meta-substituted anilines are present.
Article
Chemistry, Multidisciplinary
Shashank Shandilya, Manash Protim Gogoi, Shubham Dutta, Akhila K. Sahoo
Summary: Ynamide, a unique species with inherited polarization of nitrogen lone pair electron to triple bond, has been widely used for the development of novel synthetic methods and the construction of unusual N-bearing heterocycles. This review provides an overall scenic view into the gold catalyzed transformation of ynamides, including their reactivity towards various transfer reagents and carbon nucleophiles.
Review
Chemistry, Organic
Lucas Pages, Racha Abed Ali Abdine, Florian Monnier, Marc Taillefer
Summary: This article introduces the widespread exploration of intermolecular transition-metal catalyzed hydroarylation of allenes since the early 1980s. This reaction allows the selective access to high-value allylic or vinylic motifs through the formation of C-C bonds. The article also mentions the use of arenes, organoboronic derivatives, and aryl halides as aryl sources, as well as the use of gold, palladium, and other transition metals as catalysts.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Feifei He, Shangbiao Feng, Yulong Zhao, Hongliang Shi, Xiaoguang Duan, Huilin Li, Xingang Xie, Xuegong She
Summary: A gold-catalyzed reaction is developed to access tricyclic cores using the commonly shared bicyclic decahydroquinoline motif. These cores are then used for the divergent total syntheses of five Lycopodium alkaloids in a concise manner. Key transformations include ring cyclization, hydration, fragmentation, and construction of specific motifs.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Tingrui Li, Yilitabaier Julaiti, Xiaopeng Wu, Jie Han, Jin Xie
Summary: The gold-catalyzed ring-opening rearrangement of cyclopropenes provides an efficient method for synthesizing polysubstituted naphthols or aryl-substituted furans. The reaction selectivity between naphthols and furans can be switched by using different gold-carbenes or gold-carbocations as catalysts.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Nicola Camedda, Franca Bigi, Raimondo Maggi, Giovanni Maestri
Summary: A sequential strategy enables the challenging assembly of dihydronaphthalenes through the key annulation of an alkyne with a vinylarene under mild conditions. The products are obtained in good yields and exhibit high functional tolerance, thanks to the domino nucleophilic substitution and dearomative Diels-Alder and ene reactions. DFT modeling data suggest that alkali cations play a crucial role in ensuring a smooth dearomative cyclization of the in situ generated intermediates.
Article
Chemistry, Organic
Shivani Choudhary, Nayan Gayyur, Nayan Ghosh
Summary: A novel ynamide scaffold was designed, synthesized, and applied to a gold-catalyzed and para-toluenesulfonic acid (PTSA)-assisted cascade cycloisomerization reaction for the synthesis of beta-pyrrole substituted alpha,beta-unsaturated ketones. The reaction exhibited stereoselectivity, with the E-isomer as the major product in low to moderate yield.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Veronique Michelet
Summary: The field of gold catalysis has been expanding continuously over the past 20 years, with the discovery of several new rearrangements. Key contributions in this area include the pi-activation of unsaturated substrates and the application of aryl, alkyne, alkene, or keto derivatives.
Article
Chemistry, Applied
Philipp M. Stein, Matthias Rudolph, A. Stephen K. Hashmi
Summary: Water has an impact on the rate constant of gold-catalyzed reactions, not only showing tolerance but also potentially promoting reactions in some cases. Kinetic data demonstrates that the addition of water in gold catalysis can lead to better results.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Ryo Murakami, Hiroto Tanishima, Daisuke Naito, Hikari Kawamitsu, Ryoya Kamo, Ayaka Uchida, Kazuki Kawasaki, Chihiro Kiyohara, Motoki Matsuo, Kakeru Maeda, Fuyuhiko Inagaki
Summary: The study synthesized a cationic catalyst Au(DPB)X-3 with a specific ligand, which was successfully utilized in a specific reaction of yne-indoles.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Zhong-Lin Tao, Alafate Adili, Hong-Cheng Shen, Zhi-Yong Han, Liu-Zhu Gong
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2016)
Article
Chemistry, Multidisciplinary
Hong-Cheng Shen, Yu-Feng Wu, Ying Zhang, Lian-Feng Fan, Zhi-Yong Han, Liu-Zhu Gong
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Multidisciplinary
Tao Fan, Hong-Cheng Shen, Zhi-Yong Han, Liu-Zhu Gong
CHINESE JOURNAL OF CHEMISTRY
(2019)
Article
Chemistry, Physical
Hong-Cheng Shen, Ling Zhang, Shu-Sen Chen, Jiajie Feng, Bo-Wen Zhang, Ying Zhang, Xinhao Zhang, Yun-Dong Wu, Liu-Zhu Gong
Article
Chemistry, Organic
Tao Zhang, Hong-Cheng Shen, Jia-Cheng Xu, Tao Fan, Zhi-Yong Han, Liu-Zhu Gong
Article
Chemistry, Organic
Mostafa Sayed, Hong-Cheng Shen, Ling Zhang, Liu-Zhu Gong
SYNTHESIS-STUTTGART
(2020)
Article
Chemistry, Organic
Tao Zhang, Wen-Ao Li, Hong-Cheng Shen, Shu-Sen Chen, Zhi-Yong Han
Summary: An asymmetric Heck-Matsuda reaction targeting acyclic internal alkenes was successfully developed through the strategy of chiral anion phase transfer, resulting in high levels of enantioselectivity in the formation of chiral ketones. The use of a catalytic amount of dimethyl sulfoxide (DMSO) as an additive is crucial for suppressing palladium-hydride-mediated side reactions.
Article
Chemistry, Physical
Wen-Qian Zhang, Hong-Cheng Shen
Summary: All-carbon quaternary stereocenters are important components of natural products and bioactive compounds, and a nickel and chiral amine cooperative catalysis has been disclosed to enable highly enantioselective allylic alkylation reactions. This method allows for the synthesis of diverse compounds with excellent enantioselectivity, and has been demonstrated in the synthesis of key chiral building blocks for bioactive compounds such as (+)-eptazocine and (-)-aphanorphine.
Article
Chemistry, Multidisciplinary
Hong-Cheng Shen, Ying Chen, Ying Zhang, He-Ming Jiang, Wen-Qian Zhang, Wen-Ao Li, Mostafa Sayed, Xinhao Zhang, Yun-Dong Wu, Liu-Zhu Gong
Summary: The study demonstrates a nickel-catalyzed enantioselective desymmetrizing aza-Heck cyclization, utilizing a pentafluorobenzoyl leaving group and chiral pybox ligand, with a competitive E2-like pathway and beta-H elimination at the enantioselectivity determining step.
Article
Chemistry, Organic
Wen-Qian Zhang, Hong-Cheng Shen, Liu-Zhu Gong
Summary: A nickel/Lewis acid cooperatively catalyzed intramolecular dearomative arylcyanation of indoles is reported. The reaction involves C-CN bond activation, dearomatization, and benzylic cyanation, leading to 3-cyano fused indolinyl heterocycles with good to excellent yields and diastereoselectivity. The asymmetric version of the reaction can also be achieved with moderate enantioselectivity using a chiral ligand.
Article
Chemistry, Multidisciplinary
Hong-Cheng Shen, Mihai V. Popescu, Ze-Shu Wang, Louis de Lescure, Adam Noble, Robert S. Paton, Varinder K. Aggarwal
Summary: We report an iridium-catalyzed asymmetric alkylation-induced 1,2-metalate rearrangement of bicyclo[1.1.0]butyl boronate complexes enabled by strain release. This method allows for the asymmetric difunctionalization of C-C bonds, including dicarbonation and carboboration, providing a variety of enantioenriched three-dimensional cyclobutane products. The diastereoselectivity of the reaction has been rationalized based on experimental data and density functional theory calculations.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Ying Zhang, Hong-Cheng Shen, Yang-Yang Li, Yong-Shuang Huang, Zhi-Yong Han, Xiang Wu
CHEMICAL COMMUNICATIONS
(2019)
Article
Chemistry, Applied
Hong-Cheng Shen, Pu-Sheng Wang, Zhong-Lin Tao, Zhi-Yong Han, Liu-Zhu Gong
ADVANCED SYNTHESIS & CATALYSIS
(2017)
