Article
Chemistry, Multidisciplinary
Lin-Xuan Wang, Bin Qiu, Xiao-De An, Pei-Zhen Dong, Rui-Bin Liu, Jian Xiao
Summary: The unprecedented organocatalytic cascade aldimine condensation/[1,6]-hydride transfer/Mannich-type cyclization of indole-2-carbaldehydes with o-aminoanilines was successfully developed to assemble polycyclic indole-2,3-fused diazocanes in one step. This novel methodology is highly efficient, metal-free, redox-neutral, and capable of operating at room temperature, providing a new approach for utilizing hydride transfer chemistry in constructing medium-sized ring structures.
Review
Chemistry, Applied
Ahmad Saifuddin Mohamad Arshad, Mohd Nizam Mordi
Summary: Carbolines are a prominent class of tricyclic alkaloids found in natural products, and there are four different regioisomers known. Synthetic methods have been established for the construction of carboline frameworks, both requiring customized approaches for each regioisomer and unified approaches capable of generating multiple regioisomers. This review summarizes the construction of isomeric carbolines based on unified synthetic approaches.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Johannes Grosskopf, Alexandra A. Heidecker, Thorsten Bach
Summary: Racemic 3-substituted oxindoles can be converted into enantiomerically pure or enriched material through photochemical deracemization process. Light energy compensates for the loss of entropy and enables predictable editing of the stereogenic center. The obtained oxindoles are valuable intermediates for further transformations with complete retention at the stereogenic center.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Johannes Grosskopf, Manuel Plaza, Roger Jan Kutta, Patrick Nuernberger, Thorsten Bach
Summary: 2,5-Diketopiperazines are cyclic dipeptides with a wide range of applications, and their enantioselective preparation can be achieved through photochemical deracemization, allowing for stereochemical editing at a single position while maintaining other stereogenic centers unaffected. The chiral benzophenone catalyst in combination with irradiation at lambda=366 nm enables the establishment of configuration at the stereogenic carbon atom C6 at will.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Multidisciplinary
Takashi Koike, Munetaka Akita
Summary: The electron is unique and has the ability to participate in various systems, with novel electron injection methods revolutionizing chemical bond formation techniques in organic synthesis. In particular, visible-light organic photoredox catalysis has rapidly spread among synthetic chemists due to its sustainability and versatility.
TRENDS IN CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yannic Pilopp, Jonas Bresien, Daniel T. Gschwind, Alexander Villinger, Dirk Michalik, Axel Schulz
Summary: Differently substituted phenyl isonitriles and naphthyl isonitriles reacted with the cyclic biradical [P-*(mu-N-Ter)(2)P-*] (1) to form cyclic five-membered biradicals [P-*(NTer)2C(R)P-*] (2R, R= phenyl, naphthyl). C-H activation at the aryl substituent led to the formation of novel azaphospholes (5R), which were fully characterized. The addition of a second equivalent of isonitrile prevented the formation of azaphospholes by blocking the radical centers in 2R through adduct formation (3R). Quantum mechanical calculations revealed an increase in aromaticity as one of the driving forces for the activation process.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Jenna L. Miller, Krishnan Damodaran, Paul E. Floreancig
Summary: This manuscript describes a protocol to form acyliminium ions and related species through hydride abstractions of easily accessible allylic carbamates, amides, and sulfonamides. These intermediates are used in the synthesis of nitrogen-containing heterocycles, demonstrating high levels of stereocontrol. Areas of investigation include oxidation efficiency, geometry of intermediate iminium ions, substrate stereocenter impact on stereocontrol, and transition state geometry.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Applied
Amalia-Sofia Piticari, Daniele Antermite, Joe Higham, J. Harry Moore, Matthew P. Webster, James A. Bull
Summary: This study achieved the selective Pd-catalyzed C-H cis-functionalization of piperidine and tetrahydropyran carboxylic acids using a C(4) aminoquinoline amide auxiliary. High mono- and cis-selectivity was obtained by adding mesityl carboxylic acid. The reaction conditions developed in this study had significantly lower temperatures compared to other reported heterocycle C(sp(3))-H functionalization reactions, and a one-pot C-H functionalization-epimerization procedure was established to directly obtain the trans-3,4-disubstituted isomers. Diverse aminoquinoline removals were achieved by installing carboxylic acid, alcohol, amide, and nitrile functional groups. Overall, fragment compounds suitable for screening were synthesized in 3-4 steps from readily-available heterocyclic carboxylic acids.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Review
Chemistry, Applied
Roman S. Malykhin, Alexey Yu Sukhorukov
Summary: The review summarizes recent advances in the synthesis of C2-halogenated nitrogen heterocycles via nucleophilic halogenation of corresponding N-oxides and its application in pharmaceutical synthesis. It provides a practical guide based on extensive literature analysis to help practitioners choose optimal reagents/conditions for nucleophilic halogenation of N-heterocycles of different types. The bibliography contains 199 references.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Mohammed Sharique, Jadab Majhi, Roshan K. Dhungana, Lisa Marie Kammer, Matthias Krumb, Alexander Lipp, Eugenie Romero, Gary A. Molander
Summary: In this study, a simple, open-air, and efficient light-mediated Minisci C-H alkylation method is described, which is based on the formation of an electron donor-acceptor complex. Unlike previous protocols, this method does not require a photocatalyst, single electron transfer agent, or oxidant additive. The reaction can proceed under mildly acidic and open-air conditions, and it yields moderate to good amounts of Minisci alkylation products.
Article
Chemistry, Organic
Yu Zheng, Tianting Ma, Bingcong Liu, Shenlin Huang
Summary: A direct and efficient method for the synthesis of 3-chloro-2-formylindoles using SO2ClF is reported. This tandem system involves electrophilic chlorination, deprotonation, nucleophilic addition, and oxidation. Under mild conditions, various 2-methylindoles can be successfully transformed into 2,3-difunctionalized indoles in good yields.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Andres Arribas, Martin Calvelo, David F. Fernandez, Catarina A. B. Rodrigues, Jose L. Mascarenas, Fernando Lopez
Summary: The study presents a versatile and highly enantioselective intramolecular hydrocarbonation reaction for the synthesis of heteropolycyclic systems with chiral quaternary carbon stereocenters. The method relies on an iridium-(I)/bisphosphine chiral catalyst, yielding fused indole and pyrrole products with high enantiomeric excesses. DFT computational studies provided a detailed mechanistic profile and identified weak non-covalent interactions as key factors controlling the enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Xiang-Ting Min, Ding-Wei Ji, Yu-Qing Guan, Shi-Yu Guo, Yan-Cheng Hu, Boshun Wan, Qing-An Chen
Summary: Transition metal catalyzed decarbonylation offers a unique synthetic strategy for new chemical bond formation. The study developed a visible light induced rhodium catalysis for decarbonylative coupling of imides with alkynes under ambient conditions, revealing the rhodium complex serves as both the catalytic center and photosensitizer. This visible light promoted catalytic decarbonylation strategy opens up new opportunities for re-evaluating old transformations with ligand dissociation as a rate-determining step.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Subrata Sahoo, Shantanu Pal
Summary: An efficient and atom-economical palladium-catalyzed intramolecular cross dehydrogenative coupling (CDC) reaction has been developed for constructing highly pi-conjugated compounds using molecular oxygen as sole oxidant. The method has wide substrate scope, good functional group tolerance, and can generate fluorescence active compounds with high quantum yield. Additionally, the synthetic versatility of the method is showcased through Fe-catalyzed reductive isoxazole ring cleavage towards heteropolycyclic compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Inorganic & Nuclear
Olaya Bernardo, Silvia Gonzalez-Pelayo, Luis A. Lopez
Summary: The marriage of heterocyclic compounds with ferrocene has been a fruitful field of research, with several ferrocene-embedded heterocyclic compounds reported in recent years. The synergistic combination of properties from both heterocyclic and metallacyclic motifs in fused systems has led to interesting applications, particularly in asymmetric catalysis.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2022)
Review
Biochemistry & Molecular Biology
Dong Wang, Redouane Tabti, Sabria Elderwish, Hussein Abou-Hamdan, Amel Djehal, Peng Yu, Hajime Yurugi, Krishnaraj Rajalingam, Canan G. Nebigil, Laurent Desaubry
CELLULAR AND MOLECULAR LIFE SCIENCES
(2020)
Article
Biochemistry & Molecular Biology
Xin Jin, Jianling Xie, Michael Zabolocki, Xuemin Wang, Tao Jiang, Dong Wang, Laurent Desaubry, Cedric Bardy, Christopher G. Proud
JOURNAL OF BIOLOGICAL CHEMISTRY
(2020)
Article
Chemistry, Organic
Dong Wang, Yuanyang Jiang, Linru Dong, Gaoyu Li, Baoying Sun, Laurent Desaubry, Peng Yu
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Chunsheng Fu, Gaoyu Li, Meng Shen, Longxia Zhang, Peng Yu, Dong Wang
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Applied
Lianbo Zhao, Lei Hao, Yupeng Fu, Yan Cheng, Guojun Pan, Laurent Desaubry, Peng Yu, Dong Wang
ADVANCED SYNTHESIS & CATALYSIS
(2020)
Article
Chemistry, Organic
Linru Dong, Xinyue Ma, Yu Fan, Dong Wang
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Oncology
Tian Zhao, Yujie Liu, Yanfei Hao, Wei Zhang, Li Tao, Dong Wang, Yuyin Li, Zhenxing Liu, Edward A. McKenzie, Qing Zhao, Aipo Diao
Summary: Legumain is a newly discovered lysosomal cysteine protease that plays crucial roles in regulating immunity and cancer metastasis. Esomeprazole and omeprazole have been identified as novel legumain inhibitors, showing potential in reducing cancer cell invasion and metastasis.
INVESTIGATIONAL NEW DRUGS
(2021)
Article
Chemistry, Organic
Dong Wang, Mindong Huang, Gaoyu Li, Shixin Zheng, Peng Yu
Article
Chemistry, Multidisciplinary
Shixin Zheng, Dong Wang, Mindong Huang, Peng Yu
Summary: The method involves dearomative functionalization of pyridines or quinolines to generate amino nitrile intermediates, which then react rapidly with various Grignard reagents to synthesize novel compounds. It is characterized by being rapid, practical, and scalable.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Applied
Dong Wang, Liqing Xu, Shixin Zheng, Xiaolong Yang
Summary: This study reports a method for the di- or trifunctionalization of readily available pyridines through dearomative functionalization-oxidative rearomatization, under transition-metal- and reductant-free conditions. Computational studies provide detailed insights into the distinct reactivity of different pyridine substrates in this reaction.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Medicinal
Nora Chouha, Hussein Abou-Hamdan, Hajime Yurugi, Riku Yoshii, Hiromi Ii, Ahmad Najem, Ghanem E. Ghanem, Susumu Nakata, Krishnaraj Rajalingam, Yu Peng, Dong Wang, Canan G. Nebigil, Laurent Desaubry
Summary: This study reports the structural requirements of fluorizoline analogues for their activities. Some compounds were found to have enhanced anti-C-RAF and anti-MEK activities, and higher cytotoxicity in HeLa cells compared to fluorizoline. These findings provide a foundation for further optimization of PHB ligands for cancer treatment and the discovery of a new chemical tool to study PHB signaling in cancers and other diseases.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Medicinal
Dong Wang, Redouane Tabti, Sabria Elderwish, Amel Djehal, Nora Chouha, Franck Pinot, Peng Yu, Canan G. Nebigil, Laurent Desaubry
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2020)
Article
Chemistry, Multidisciplinary
Dong Wang, Yu Fan, Peng Yu, Laurent Desaubry
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Dong Wang, Zhenlin Liu, Zhentao Wang, Xinyue Ma, Peng Yu