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
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.
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, 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, Organic
Haofan Ji, Phil C. Knutson, Christopher M. Harrington, Yan-Ting Ke, Eric M. Ferreira
Summary: This article describes a comprehensive and enantioselective total synthesis of (+)-gelsenicine. Two different strategies based on catalytic cycloisomerization as the central step are proposed. One strategy involves chirality transfer from enantioenriched substrates, while the other employs asymmetric catalysis. The chirality transfer strategy is less effective, whereas the latter strategy utilizes phosphoramidite- and bisphosphine-gold complexes to provide a high enantiopurity key intermediate in the Gelsemium alkaloid syntheses. (c) 2023 Elsevier Ltd. All rights reserved.
Article
Chemistry, Applied
Romeric Galea, Gaelle Blond
Summary: In this study, [7,5]-fused bicyclic acetals, also known as furooxepines, were synthesized through a gold(I)-catalyzed domino reaction. This one-step reaction allows the formation of multiple bonds, heterocycles, and a tetrasubstituted carbon stereocenter with 100% atom economy.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Review
Chemistry, Multidisciplinary
Chandrasekar Praveen
Summary: This article focuses on the regioselective cycloisomerization of structurally distinctive pi-connected hetero-nucleophiles catalyzed by gold, leading to the construction of different heterocycles. It also discusses the application of these methodologies in the total synthesis of natural products, along with the contributing factors for selectivity.
Article
Chemistry, Multidisciplinary
Chuan Xiang Alvin Tan, Rui Li, Fuhao Zhang, Lei Dai, Nisar Ullah, Yixin Lu
Summary: A sequential phosphine-catalyzed asymmetric [3+2] annulation of aldimines has been developed, utilizing an oxidative central-to-axial chirality transfer strategy. This approach is operationally simple and allows for the rapid synthesis of highly enantioselective 2-arylpyrroles.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Xuemeng Jing, Fangyu Fu, Ruijie Wang, Xing Xin, Lin Qin, Hongjin Lv, Guo-Yu Yang
Summary: In this work, a pair of atomically precise enantiomers of silver clusters were synthesized, and their chirality was attributed to the asymmetric arrangement of surface ligands. These clusters could form two-dimensional assemblies, exhibiting excellent thermal stability and photocatalytic activity, providing possibilities for exploring catalysts based on fixed coinage clusters with attractive properties.
Article
Chemistry, Multidisciplinary
K. Vipin Raj, Pawan S. S. Dhote, Kumar Vanka, Chepuri V. V. Ramana
Summary: Gold catalysis is a promising area of research in organic synthesis in this century, with a focus on reactions involving alpha-oxo gold carbene/alpha-imino gold carbene intermediates. This manuscript documents theoretical investigations on the regio-selectivity dependence of substitution in the gold-catalyzed cycloisomerization of o-nitroarylalkyne derivatives, as well as the relative stabilities of alpha-oxo gold carbene intermediates.
FRONTIERS IN CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Lenka Pallova, Laura Abella, Marion Jean, Nicolas Vanthuyne, Cecile Barthes, Laure Vendier, Jochen Autschbach, Jeanne Crassous, Stephanie Bastin, Vincent Cesar
Summary: The first efficient chiral helicene-NHC gold(I) complexes for enantioselective catalysis have been synthesized. Their structural and stereochemical characterization confirms their potential in asymmetric catalysis, demonstrated by the benchmark cycloisomerization reaction with high enantiomeric excess.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Eduardo Garcia-Padilla, Imma Escofet, Feliu Maseras, Antonio M. Echavarren
Summary: Through computational analysis, we have identified the dominant structures of the intermediates of gold(I)-catalyzed cyclizations of 1,5-enynes and 1,5-allenenes, including gold(I) cyclopropylcarbenes, endocyclic vinylgold complexes and previously unreported non-classical carbocationic minima. Cyclopropylcarbene structures are consistently favored as the most stable intermediates for all studied substitution patterns.
Article
Chemistry, Inorganic & Nuclear
Jacopo Segato, Walter Baratta, Paola Belanzoni, Leonardo Belpassi, Alessandro Del Zotto, Daniele Zuccaccia
Summary: The study showed that the activity of NHC-Au-X catalysts in the cycloisomerization of N-(prop-2-yn-yl)benzamide is related to the basic strength of the anion, with performance decreasing gradually with increasing basicity and hydrogen-bond acceptor power of X-. The characteristics of the solvent and counterion should both be taken into account in considering the reaction.
INORGANICA CHIMICA ACTA
(2021)
