Article
Chemistry, Multidisciplinary
Juan Du, Yun-Fan Li, Chang-Hua Ding
Summary: Palladium-catalyzed cycloaddition reactions using Pd-p-allyl zwitterions are significant synthetic transformations for the construction of carbon- or heterocycles compounds found in biologically active natural products and pharmaceuticals. Recent studies have explored new applications of previously less-studied Pd-p-allyl zwitterions and designed impressive novel zwitterions, which are diverse and highly reactive intermediates for the synthesis of complex polycyclics and medium-sized cyclic compounds.
CHINESE CHEMICAL LETTERS
(2023)
Review
Chemistry, Applied
Ricardo Toran, Ruben Miguelez, Amparo Sanz-Marco, Carlos Vila, Jose R. Pedro, Gonzalo Blay
Summary: Five-membered heterocycles bearing an exocyclic double bond have been used successfully as substrates in asymmetric addition and cycloaddition reactions. Ylidene-heterocycles are attractive substrates due to their high functionalization and presence of an electrophilic conjugated exocyclic double bond.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Yulin Han, Anni Qin, Qian Zhang, Xue Zhang, Hui Qian, Shengming Ma
Summary: The Rh-catalyzed reaction allows for the efficient synthesis of cis-fused bicyclic products with excellent selectivity and tolerance towards synthetically useful functional groups. The proposed mechanism involves the rapid racemization of the allene moiety in the starting materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
John M. Halford-McGuff, Alexandra M. Z. Slawin, Allan J. B. Watson
Summary: This article presents a predictive model for the reactivity and turnover of the Rh-catalyzed [2 + 2 + 2] cycloaddition of diynes and alkynes. Contrary to the proposed electronic model, this model suggests that the reaction is predominantly driven by steric effects, and turnover is proportional to alkyne steric parameters. The model allows for the prediction of catalyst loading, turnover, and reaction yield based on the assessment of the alkyne's steric parameter.
Article
Chemistry, Organic
Tao Liu, Lingli Han, Jing Zhang, Gang Lu
Summary: Density functional theory calculations were used to investigate the competing pathways of rhodacycle intermediates in Rh(III)-catalyzed annulations of 2-alkenyl phenols and 2-alkenyl anilides with alkynes. The results reveal that the multiple pathways of eight-membered rhodacycles can be subtly tuned to give specific cyclic products. The formation of different cyclic products from 2-alkenyl phenols and 2-alkenyl anilides is governed by different pathways involving the dissociation of Rh-O bond and intramolecular olefin migratory insertion, respectively.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Marc Strohmann, Andreas J. Vorholt, Walter Leitner
Summary: This study presents a method for transforming olefins into branched amines by combining hydroformylation/aldol condensation tandem reaction with reductive amination. The method utilizes a combined multiphase system that can be recycled 9 times. The study demonstrates the feasibility of the method and its potential applications in the production of surfactants.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Wenxiang Wang, Chao Pi, Xiuling Cui, Yangjie Wu
Summary: A TBAI-catalysed [4+4]-cyclization reaction was developed for the synthesis of oxa-bridged eight-membered heterocycles from anthranils and hydrazones. Mechanistic studies showed the in situ generation of vinyldiazenes from hydrazones, followed by an aza-Michael addition and subsequent annulation. This strategy overcomes the limitations of anthranils in organic chemistry and provides a high efficiency and atom economical approach.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Review
Chemistry, Multidisciplinary
Deepak R. Mishra, Bhabani S. Panda, Sabita Nayak, Jasmine Panda, Seetaram Mohapatra
Summary: This review summarizes the significant progress and advances in the synthesis of 5-membered N-heterocycles through rhodium-catalyzed cascade reactions, including annulations, C-H/C-C activation, cycloaddition, rearrangement, cyclization, and metathesis, from 2018 to 2021.
Article
Biochemistry & Molecular Biology
Sofia Siciliano, Elena Cini, Maurizio Taddei, Giorgia Vinciarelli
Summary: The synthesis of 2-substituted indoles from unprotected 2-alkynylanilines using Pd(OAc)(2) catalyst in 3% TPGS-750-M water was found to be sensitive to the heating mode and the MW delivery mode, with convectional heating often proving more effective than microwave dielectric heating. Additionally, a tandem Sonogashira-cyclisation reaction was successfully achieved in the nanomicellar water environment with Pd(OAc)(2)/Xphos.
Review
Chemistry, Organic
Anae I. Bain, Kiran Chinthapally, Arianne C. Hunter, Indrajeet Sharma
Summary: Dual catalysis is a more efficient method in carbene chemistry that improves the efficiency of existing reactions and enables new chemical transformations. Reactions involving dual synergistic catalysis offer convenient strategies for synthesizing challenging quaternary carbon centers and bioactive core structures.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Athanasios Markos, Vaclay Matousek, Petr Beier
Summary: Fluorinated azidoalkanes are novel and stable azides that are easily prepared and commercially available, offering new possibilities for their application in organic synthesis. This review focuses on the use of fluorinated azidoalkanes in cycloaddition reactions to produce N-fluoroalkyl-1,2,3-triazoles, as well as the transformations of these triazoles via rhodium-catalysis and acid-mediated reactions to obtain diverse N-fluoroalkyl nitrogen heterocycles and N-alkenyl compounds.
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)
Article
Chemistry, Physical
Xin-Shen Liang, Rui-Dong Li, Wei Sun, Zhong Liu, Xiao-Chen Wang
Summary: Borane-mediated hydride abstraction has been shown to be a powerful tool for the C(sp(3))-H functionalization of amines, but its activity with ethers is still unknown. In this study, we discovered this activity in 2H-chromenes and established a catalytic C(sp(3))-H functionalization reaction using silyl ketene acetals as nucleophiles.
Review
Chemistry, Organic
Navjeet Kaur, Neha Ahlawat, Yamini Verma, Pooja Grewal, Pranshu Bhardwaj, Nirmala Kumari Jangid
Summary: Metal-mediated formation of heterocycles is an emerging and important strategy in organic chemistry. Silver-assisted cyclic reactions are highly efficient for the synthesis of five-membered fused N-heterocyclic compounds. This review article covers the applications of silver in the preparation of these compounds.
CURRENT ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Guoqiang Yang, Ya-Ming Ke, Yu Zhao
Summary: A gold and palladium sequential catalysis system has been reported for efficient and enantioselective access to furan-fused nine-membered heterocycles. In this one-pot procedure, easily accessible enynamides undergo cyclization to generate azadienes in situ, which then participate in enantioselective formal [5+4] cycloaddition with vinyl ethylene carbonates. Furthermore, conformation-controlled highly diastereoselective derivatizations of these medium-sized rings, coupled with oxidative furan cleavage, have enabled the access to diverse densely-functionalized nine-membered lactams.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Ju Young Lee, Jae Yul Shim, Hong Ki Kim, Donguk Ko, Mu-Hyun Baik, Eun Jeong Yoo
JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Physical
Nirupam De, Eun Jeong Yoo
Article
Chemistry, Multidisciplinary
Nirupam De, Choong Eui Song, Do Hyun Ryu, Eun Jeong Yoo
CHEMICAL COMMUNICATIONS
(2018)
Article
Chemistry, Organic
Sushovan Paladhi, In-Soo Hwang, Eun Jeong Yoo, Do Hyun Ryu, Choong Eui Song
Article
Chemistry, Organic
Hui Jin, Juyeol Lee, Hu Shi, Jin Yong Lee, Eun Jeong Yoo, Choong Eui Song, Do Hyun Ryu
Article
Chemistry, Physical
Seung-yeol Baek, Ju Young Lee, Donguk Ko, Mu-Hyun Baik, Eun Jeong Yoo
Article
Chemistry, Organic
Donguk Ko, Seung-yeol Baek, Jae Yul Shim, Ju Young Lee, Mu-Hyun Baik, Eun Jeong Yoo
Article
Chemistry, Organic
Ju Young Lee, Jiyoung Kim, Ji Hye Lee, Hyonseok Hwang, Eun Jeong Yoo
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Physical
Nirupam De, Donguk Ko, Seung-yeol Baek, Changjin Oh, Jiyoung Kim, Mu-Hyun Baik, Eun Jeong Yoo
Article
Chemistry, Organic
Jiyoung Kim, Eun Jeong Yoo
Summary: By carefully controlling the reaction kinetics and utilizing a silver catalyst, a catalytic ring expansion of activated heteroarenes was achieved through 1,4-dearomative addition to construct fused azepines. The developed methodology offers an innovative approach for the synthesis of biologically relevant multifused azepines, showcasing excellent substrate scope and selectivity.
Article
Chemistry, Organic
Ju Young Lee, Srinivas Samala, Jiyoung Kim, Eun Jeong Yoo
Summary: This study describes the valence tautomerizations of fused 1,4-diazepines yielding pyrrole derivatives and HCN gas by elucidating factors influencing the equilibrium between different valence tautomers of an 8 pi-electron diazepine skeleton. A cascade strategy for constructing diazepines followed by ring contraction is developed, leading to aryl- or alkyl-substituted pyrrolo[1,2-a]quinolines, and the advantages of this methodology are highlighted through further transformations of the obtained products.
Article
Chemistry, Organic
Ju Young Lee, Rohit Kumar Varshnaya, Eun Jeong Yoo
Summary: This study reported a copper-catalyzed [5+3] cycloaddition reaction for the synthesis of enantio-enriched diazocine derivatives. It was found that specific ligands and additives played significant roles in the catalytic process and preserved the induced stereoselectivity, demonstrating the potential applications of this asymmetric catalysis.
Article
Chemistry, Organic
Sekwang Baek, Hyundug Jen, Eun Jeong Yoo
Summary: In this study, a silver-catalyzed reaction was developed for the construction of phosphorus-containing azepine derivatives via a domino-type dearomatization procedure followed by ring expansion. Additionally, diazomethylphosphonates were used for the first time as nucleophiles in the 1,4-dearomative addition of activated N-heteroarenes, providing cyclopropane-fused piperidine intermediates that could be easily restructured into their corresponding azepine derivatives. The reactivities of diazomethylphosphonates in the developed dearomatization strategy were superior to other diazo compounds, leading to the formation of desired seven-membered N-heterocycles in a very short reaction time.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Multidisciplinary
Jiyoun Lee, Donguk Ko, Hyunju Park, Eun Jeong Yoo
Article
Chemistry, Organic
Srinivas Samala, Do Hyun Ryu, Choong Eui Song, Eun Jeong Yoo
ORGANIC & BIOMOLECULAR CHEMISTRY
(2019)
