Article
Chemistry, Multidisciplinary
Wei Huang, Jiahui Bai, Yinlong Guo, Qinglei Chong, Fanke Meng
Summary: A catalytic enantioselective coupling of 1,1-disubstituted allenes and aldehydes is achieved through regiodivergent oxidative cyclization followed by stereoselective protonation or reductive elimination promoted by chiral phosphine-Co complexes. This unprecedented reaction pathway for Co catalysis allows for the catalytic enantioselective generation of metallacycles with divergent regioselectivity accurately controlled by chiral ligands, leading to a wide range of allylic alcohols and homoallylic alcohols in high yields and excellent regioselectivity, diastereoselectivity, and enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Ke Zhao, Philip Kohnke, Ziguang Yang, Xinpeng Cheng, Shu-Li You, Liming Zhang
Summary: A gold(I)-catalyzed enantioselective dearomatization is achieved through metal-chiral ligand cooperation. A new and divergent synthesis of chiral bifunctional binaphthyl-2-ylphosphines is developed for rapid access to these ligands, enabling broad substrate scope. The selective acceleration of one enantiomer formation is achieved through hydrogen bonding between substrate and ligand remote basic group, leading to enantiomeric excesses up to 98%.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Yongliang Zhang, Ke Zhao, Xinyi Li, Carlos D. Quintanilla, Liming Zhang
Summary: By using a chiral bifunctional phosphine ligand, a highly efficient and enantioselective dearomatization of phenols is achieved through metal-ligand cooperation. The reaction shows great generality by allowing substitutions at various positions of benzene, including electron-withdrawing groups and carbon-based groups. Spirocyclohexadienone-pyrrol-2-ones, spirocyclohexadienone-butenolides, and spirocyclohexadenone-cyclopentenones are formed in high yields and with high enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Pawan S. Dhote, Swapnil V. Halnor, Chepuri V. Ramana
Summary: The article discusses the gold-catalysed intramolecular redox cyclization of o-alkynylnitrobenzens, highlighting its importance and potential for further research in metal catalysis. It also touches upon the idea of generating alpha-oxo gold carbenes via oxygen transfer to alkynes, establishing another significant aspect in gold catalysis.
Article
Chemistry, Organic
Dae-Kwon Kim, Minjung Keum, Heekyung Yun, Insu Kim, Jung Min Joo, Chulbom Lee
Summary: Here, we describe a rhodium-catalyzed oxygenative carbofunctionalization of terminal alkynes that leads to the regioselective quadruple formation of C-C, C-H, C-O, and C-heteroatom bonds. Mechanistic studies reveal that a disubstituted rhodium vinylidene complex is formed upon C-C bond formation, followed by intermolecular transfer oxygenation and reaction with heteroatom nucleophiles to generate cyclic carboxylic acid derivatives.
Article
Chemistry, Applied
Christoph M. Hendrich, Valentin D. Hannibal, Lukas Eberle, Leif E. Hertwig, Ute Zschieschang, Frank Rominger, Matthias Rudolph, Hagen Klauk, A. Stephen K. Hashmi
Summary: This study presents a gold-catalyzed bidirectional synthesis method for N-heteropolycyclic compounds bearing carbazole moieties, resulting in the synthesis of four previously unknown core structures. The approach is convergent and modular, with a key step involving a gold-catalyzed cascade reaction starting from stable di-azido compounds. The synthesized molecules were fully characterized, and their optical and electronic properties, as well as their performance in organic thin-film transistors generated by vacuum deposition, were studied, with charge-carrier mobilities of up to 0.3 cm(2)/Vs measured.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Review
Chemistry, Multidisciplinary
Ashanul Haque, Khalaf M. Alenezi, Muhammad S. Khan, Wai-Yeung Wong, Paul R. Raithby
Summary: The design and development of functional materials with practical applications require high standards. Understanding and controlling inter- and intra-molecular interactions offer opportunities for designing new materials. Manipulating the molecular structure can significantly alter these interactions and enhance the properties and functions of the material. Non-covalent interactions (NCIs) have been found to have beneficial effects, indicating that manipulating NCIs can generate functional materials with various physical properties for applications in catalysis, drug delivery, crystal engineering, etc. This review aims to explore the implications of NCIs on molecular packing, optical properties, and applications of functional pi-conjugated materials. Additionally, it attempts to delineate the effects of weak interactions on opto-electronic (O-E) applications.
CHEMICAL SOCIETY REVIEWS
(2023)
Article
Chemistry, Physical
Cheng Zhang, Qiaoying Sun, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi
Summary: In this study, a new strategy is proposed for controlling the selectivity of catalytic reactions by adjusting the electronic and steric properties of metal complexes. The high regioselectivity of the reaction is achieved with the use of an additive, and a novel intramolecular cascade fluorination process is described for the synthesis of aryl fluorides.
Article
Chemistry, Multidisciplinary
Muhammad Adnan Bashir, Yulong Zhang, Huaibin Yu, Bofei Wang, Weining Zhao, Fangrui Zhong
Summary: A novel family of electron donors benzofuro[2,3-b]indoles were successfully synthesized through a bimetallic catalysis strategy involving CoCl2/Cu(OTf)2, which showed superior efficiency and potential for further research. This method outperformed traditional multi-step synthesis approaches and demonstrated promising photophysical properties for potential applications in deep-blue organic light-emitting diodes.
Article
Chemistry, Organic
Miyu Yokoyama, Yoshinori Okayasu, Yoichi Kobayashi, Hiroki Tanaka, Yohei Haketa, Hiromitsu Maeda
Summary: Dithienylnitrophenols were synthesized to form pi-electron anions, which were stabilized by intramolecular chalcogen bonding and combined with cations to form various ion pairs. The assembly modes of charge-by-charge in the solid state, along with stacking and photoinduced electron transfer behaviors in solution, were modulated by the different ionic species.
Article
Chemistry, Multidisciplinary
Ruiping Li, Mohammad Zafar, David Danovich, Vasudevan Subramaniyan, Francoise Tibika, Yuri Tulchinsky
Summary: This study demonstrates that the instability of sulfonium complexes in catalytic applications can be overcome by increasing the rigidity of the sulfonium ligand. The newly designed tris-cationic sulfonium-Pt(II) complex shows high reactivity in reactions compared to its thioether-based analogue.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Xiaoyu Hao, Tian-Ren Li, Hao Chen, Andrea Gini, Xiang Zhang, Stephane Rosset, Clement Mazet, Konrad Tiefenbacher, Stefan Matile
Summary: This study reports on how the broad responsiveness of ether cyclizations to diverse inputs helps to fill the gap in understanding the unique characteristics of system catalysts. Cyclizations within supramolecular capsules show exceptional speed and selective violations of the Baldwin rules, while cyclization on pi-acidic aromatic surfaces exhibits unique autocatalytic properties.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Teng Yuan, Qi Tang, Chuan Shan, Xiaohan Ye, Jin Wang, Pengyi Zhao, Lukasz Wojtas, Nicholas Hadler, Hao Chen, Xiaodong Shi
Summary: This study presents a novel method for alkyne trifunctionalization through gold catalysis, achieving consecutive reactions with high efficiency and excellent yields under mild conditions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Wen-Tao Zhao, Huan Meng, Jia-Ni Lin, Wei Shu
Summary: In this study, a ligand-controlled regiodivergent alkylation of alkyl bromides at different positions has been developed via Ni-catalyzed alkyl-alkyl cross-electrophile coupling with a second alkyl bromide. The reaction selectively isomerizes one alkyl bromide in a controlled manner, providing diverse alkylated structures at different sites. The reaction exhibits excellent chemo- and regioselectivity at three similar positions, showcasing the remarkable ligand-tuned reactivity between alkyl-alkyl cross-coupling and nickel migration. This reaction offers a catalytic platform for the synthesis of diverse saturated architectures from identical starting materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Hai-Yun Huang, Amal Benzai, Xinzhe Shi, Henri Doucet
Summary: Researchers are focused on developing different procedures for direct functionalization of two different C-H bonds of the same organic molecule, which is currently an important research topic in organic chemistry. Over the past decade, the number of tools to control regiodivergent C-H bond functionalizations has significantly increased.
Article
Chemistry, Organic
Ming Wang, Zongjun Qiao, Jiaoyan Zhao, Xuefeng Jiang
Article
Chemistry, Multidisciplinary
Ming Wang, Jiaoyan Zhao, Xuefeng Jiang
Article
Chemistry, Multidisciplinary
Yiming Li, S. Aal-e-Ali Rizvi, Deqing Hu, Danwen Sun, Anhui Gao, Yubo Zhou, Jia Li, Xuefeng Jiang
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Organic
Wei Tan, Niklas Jaensch, Tina Oehlmann, Franz-Josef Meyer-Almes, Xuefeng Jiang
Article
Chemistry, Multidisciplinary
Yingying Meng, Ming Wang, Xuefeng Jiang
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Minghao Feng, Joao De Oliveira, Antoine Sallustrau, Gianluca Destro, Pierre Thuery, Sebastien Roy, Thibault Cantat, Charles S. Elmore, Jorg Blankenstein, Frederic Taran, Davide Audisio
Summary: The use of carbon-14 allows for tracking of organic molecules and provides important knowledge on their fate. A new transition-metal-catalyzed procedure enables carbon isotope exchange on aromatic nitriles, reducing synthetic costs and limiting radioactive waste generation. This procedure will facilitate the labeling of nitrile-containing drugs and accelerate C-14-based ADME studies supporting drug development.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Minghao Feng, Ivan Mosiagin, Daniel Kaiser, Boris Maryasin, Nuno Maulide
Summary: This study presents a novel strategy for the diastereo- and enantioselective synthesis of fi-amino amides through the direct coupling of carboxamides with ketimines. This innovative approach addresses key challenges in the Mannich reaction process, showcasing its significance in synthetic and biological chemistry.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Review
Chemistry, Multidisciplinary
Minghao Feng, Haoqi Zhang, Nuno Maulide
Summary: Compared to ketones and carboxylic esters, amides have traditionally been considered as less reactive members of the carbonyl family. However, recent research has shown that selective activation of amides under mild conditions is possible. This Minireview highlights the latest advances in this field, showcasing new strategies and breakthroughs in amide activation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Minghao Feng, Roberto Tinelli, Ricardo Meyrelles, Leticia Gonzalez, Boris Maryasin, Nuno Maulide
Summary: This study reports a practical method for the synthesis of alpha-amino acid derivatives via direct hydrative amination of activated alkynes using sulfinamides as the nitrogen source under mild conditions. Computational studies suggest that the reaction is enabled by a new type of sulfonium [2,3]-sigmatropic rearrangement.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Minghao Feng, Anthony J. J. Fernandes, Ana Sirvent, Eleonora Spinozzi, Saad Shaaban, Nuno Maulide
Summary: We present a simple method for the direct amination of unfunctionalized, native carbonyls (amides and ketones) by transferring a free amino group (NH2) from a commercially available nitrogen source. Mild conditions enable the production of primary a-amino carbonyls, allowing for diverse in situ functionalization reactions, such as peptide coupling and Pictet-Spengler cyclization, that take advantage of the presence of the unprotected primary amine.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Minghao Feng, Lea Madegard, Margaux Riomet, Manon Louis, Pier Alexandre Champagne, Gregory Pieters, Davide Audisio, Frederic Taran
Summary: In this study, a methodology for chlorination of iminosydnones is described, and the beneficial effect of this modification on the reactivity of these mesoionic dipoles in strain-promoted cycloaddition reactions is demonstrated. The new iminosydnones are used for bioorthogonal release of drugs containing amide, urea, and sulfonamide, with notable success in releasing drugs containing a terminal amide function.
CHEMICAL COMMUNICATIONS
(2022)
Review
Biochemistry & Molecular Biology
Nengzhong Wang, Puli Saidhareddy, Xuefeng Jiang
NATURAL PRODUCT REPORTS
(2020)
Article
Chemistry, Multidisciplinary
Shihao Chen, Yaping Li, Ming Wang, Xuefeng Jiang
Article
Chemistry, Multidisciplinary
Yiming Li, Tao Mou, Lingling Lu, Xuefeng Jiang
CHEMICAL COMMUNICATIONS
(2019)
Article
Chemistry, Multidisciplinary
Ming Wang, Qiaoling Fan, Xuefeng Jiang
