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, 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, Physical
Abdoul G. Diallo, Deborah Paris, Djiby Faye, Sylvain Gaillard, Mark Lautens, Jean-Luc Renaud
Summary: This study reports a general approach for the allylation of oxa- and azabenzonorbornadienes by merging organophotoredox and nickel catalysis. The method allows for selective allylation of various heterocyclic alkene derivatives with a broader range of allylic acetate compounds. Notably, the reaction does not require air-sensitive organometallic species or metal reductants.
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.
Review
Chemistry, Multidisciplinary
Ruben Vicente
Summary: This review summarizes key reactivities relying on C-C bond cleavages of cyclopropenes, including both metal-catalyzed and metal-free transformations. The emphasis is on the synthetic utility and mechanistic aspects of various methodologies discussed, covering a range of reactions involving vinyl carbenes, metathesis processes, heterocycles syntheses, SEAr reactions, metalation-ring opening sequences, and cycloadditions. The focus is on results from 2007 to 2019, with relevant pioneering transformations eventually included.
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, Applied
Patricia Garcia-Martinez, Olaya Bernardo, Javier Borge, Javier Gonzalez, Luis A. Lopez
Summary: The BF3 & sdot;OEt2-catalyzed reaction of azulene with N-protected aziridines provides a general and efficient method for synthesizing phenethylamine-azulene conjugates with high regioselectivity (up to 91% yield). Stereochemical studies and DFT calculations confirm a concerted SN2-type mechanism for the ring-opening reaction of aziridine.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Jianhui Qiao, Huili Liu, Shaozhong Wang
Summary: A protocol has been developed for accessing indole-annulated eight- and nine-membered lactams through protonation-induced ring-opening of spiroindolines, with the use of deuterated hydrochloride and deuterated methanol resulting in medium-sized lactam diastereoisomers with a deuterium content ratio around 1:1. The study compared different Bronsted acids and nucleophiles in the transformation process.
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
Boon Beng Tan, Ming Hu, Shaozhong Ge
Summary: A ligand-controlled cobalt-catalyzed ring-opening dihydroboration method is developed to access versatile skipped diboronates. Various arylidenecyclopropanes reacted with pinacolborane to yield 1,3- or 1,4-diboronate products with high regioselectivity. The resulting diboronates can undergo various transformations, enabling selective installation of different functional groups on alkyl chains.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Feng An, Harish Jangra, Yin Wei, Min Shi, Hendrik Zipse, Armin R. Ofial
Summary: The kinetics of the reactions of tributylphosphine with allenic and olefinic Michael acceptors were studied using photometric and NMR spectroscopic methods. The relevance of retroaddition barriers in phosphine-catalysed reactions was revealed when mixtures of allenic and olefinic substrates were used.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Ben Mao, Xiao-Yu Zhang, Yin Wei, Min Shi
Summary: A concise and practical strategy for the synthesis of benzazepine derivatives has been developed through a ring-opening/cyclization cascade reaction of alpha-brominated amide-tethered alkylidenecyclopropanes in the presence of photocatalyst 4CzIPN under visible-light irradiation.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Long-Hai Li, Hao-Zhao Wei, Yin Wei, Min Shi
Summary: In this study, a strategy to overcome the limitation of the Morita-Baylis-Hillman (MBH) reaction, which is restricted to electron-deficient olefins, was achieved using visible-light induced photoredox catalysis. By employing a novel photoredox-quinuclidine dual catalysis, non-electron-deficient olefins were able to undergo the MBH reaction smoothly. Mechanistic studies, including radical probe experiments and density functional theory (DFT) calculations, were conducted to support the proposed reaction pathways.
Article
Chemistry, Organic
Zhen Liu, Yin Wei, Min Shi
Summary: This paper presents a visible-light-mediated regioselective ring-opening hydrogenolysis of donor-acceptor cyclopropanes for the synthesis of alkylated aryl ketones in moderate to excellent yields with good functional group compatibility under mild conditions. The method provides a facile and practical approach to access a variety of alkylated aryl ketones with low cost reductant. A mechanistic paradigm has been proposed based on control experiments, deuterium labeling, and H-1 NMR tracing experiments.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Review
Chemistry, Multidisciplinary
Hao-Zhao Wei, Min Shi, Yin Wei
Summary: Diverse transformations of methylenecyclopropanes (MCPs) under visible-light irradiation have attracted significant attention from synthetic chemists. MCPs, as readily accessible strained molecules, possess sufficient reactivity to selectively generate different target products through reactions with various radical species. These transformations can be classified into three subcategories, forming ring-opened products, cyclopropane derivatives, and alkynes. This review summarizes the recent advancements in this field.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Min Li, Yin Wei, Min Shi
Summary: This paper describes the development of a thermally-induced intramolecular [2 + 2] cycloaddition reaction for the rapid construction of polycyclic heterocycles. The reaction proceeds under relatively mild conditions, offering excellent total yields and good functional group compatibility. The mechanism of the reaction has been clarified through control experiments and DFT calculations, revealing a stepwise process involving a key intermediate with a seven-membered ring rather than a concerted pathway.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Applied
Jun-Sheng Wei, Zi-Yu Xu, Yin Wei, Min Shi
Summary: In this paper, a gold(I)-catalyzed cascade cyclization of N- or O-nucleophile tethered-vinylidenecyclopropanes (VDCPs) is reported, leading to the synthesis of pyrrole, furan, pyrrolidine, and piperidine skeletons in 30%-98% yields. The reaction pathways depend on the carbon chain length connecting the nucleophile and VDCPs, resulting in different products. By using α-amino VDCPs and α-hydroxyl VDCPs with a methylene group as the connection, intramolecular nucleophilic addition and aromatization occur, followed by ring-opening of the cyclopropane unit to produce substituted pyrroles and furans. Extending the chain length to three or four carbons enables the formation of pyrrolidines and piperidines with a cyclobutene moiety through ring expansion of the cyclopropane unit and gold carbene induced vinylogous nucleophilic addition.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Chemistry, Multidisciplinary
Jia-Hao Shen, Min Shi, Yin Wei
Summary: The combination of visible light photocatalysis and organocatalysis has been widely used in various reactions in recent years. The synergy between visible light photocatalysis and organocatalysis has led to significant progress in modern chemical synthesis. In these dual catalytic systems, photocatalysts or photosensitizers absorb visible light to activate unreactive substrates through electron or energy transfer mechanisms, while organocatalysts are used to control the reactivities of other substrates. This review primarily focuses on the recent advancements in cooperative catalysis by the combination of organocatalysis and photocatalysis in organic synthesis.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Hao-Zhao Wei, Yin Wei, Min Shi
Summary: In this paper, dithienylethene-based chiral bisoxazoline ligands with bidirectional photoswitching capabilities under visible light irradiation were successfully synthesized, and a strategy for adjusting the conjugation system length in sensitizer groups was proposed. The detailed experimental procedures and the characterization data can be found in the main text and the Supporting Information. Despite their moderate photoswitching rates, these ligands offer a promising approach towards developing fully visible light-responsive chiral catalysts.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Zhe Meng, Jun Yan, Chao Ning, Min Shi, Yin Wei
Summary: This paper presents an efficient synthetic strategy for the rapid construction of multisubstituted pyrroles, furans, and thiophenes via NXS mediated desulfonylative/dehydrogenative cyclization of vinylidenecyclopropanes. The method offers advantages such as a wide substrate range, high efficiency, and synthetic usefulness of the heterocyclic products under metal-free and mild conditions. The derivatization of pyrrole products and the preparation of functional molecules demonstrate the synthetic potential of the products as platform molecules. The reaction mechanism has been investigated through control experiments and DFT calculations.
Article
Chemistry, Multidisciplinary
Jun Yan, Min Shi, Yin Wei
Summary: In this minireview, the recent asymmetric cyclization of alkynes with other functional groups such as carbonyl-alkynes, cyano-alkynes, and enynes under the catalytic system of nickel and chiral ligands is mainly summarized.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Jun-Sheng Wei, Song Yang, Yin Wei, Sima Shamsaddinimotlagh, Hossein Tavakol, Min Shi
Summary: A gold(i)-catalyzed intramolecular cyclization reaction was developed to synthesize functionalized morpholines, piperazines, and oxazepanes. The reaction proceeds via a carbene or non-carbene process and exhibits a broad substrate scope, good functional group tolerance, and mild reaction conditions. The reaction pathway can be modulated by the steric bulkiness or chain length of the substrate.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Ling Qian, Min Shi
Summary: In recent years, organic synthetic chemistry has witnessed the discovery and application of various organic synthetic methods in practical production. Photochemistry and electrochemistry, due to their advantages of mild conditions and environmental protection, have become two of the most prominent synthetic strategies in organic synthesis. To further maximize their potential and overcome their limitations, organic synthetic chemists have combined these two strategies to develop photoelectrochemistry as a new synthetic method. Photoelectrochemistry combines the complementary advantages and disadvantages of photochemistry and electrochemistry, generating highly reactive intermediates under mild conditions and enabling reactions that are difficult to accomplish with single photochemistry or electrochemistry. This review summarizes the recent research progress in the field of photoelectrochemistry from the perspective of photoelectrochemical catalysts, analyzes the catalytic mechanisms of various catalysts, and provides a brief outlook on the research direction and development prospects in this field.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Jun Yan, Ziqi Yu, Hao-Zhao Wei, Min Shi, Yin Wei
Summary: In this paper, a photochemical strategy for the efficient conversion of (2-vinylaryl)methanol derivatives to aryl aldehydes or aryl ketones under visible light-mediated conditions was reported. The reaction mechanism involving triplet state formation of olefins, 1,5-hydrogen atom transfer, enol tautomerization, and proton transfer was supported by various experimental and computational studies.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Yan-Shun Zhang, Yin Wei, Min Shi
Summary: This study presents a sequential dual catalytic transformation for the rapid synthesis of polysubstituted caged oxa-bishomocubane products. The method is simple and utilizes readily available starting materials, providing good step-economy.
ORGANIC CHEMISTRY FRONTIERS
(2022)
