Article
Chemistry, Multidisciplinary
Ashmita Singh, A. K. Narula
Summary: A facile method for the amidation of aldehydes by a cascade approach has been developed using NHC as the catalyst and NHS as the mediator. The method utilizes TBHP as the oxidant. Various substituted aldehydes reacted smoothly with NHS to form active esters, which were easily converted into amides. The drug moclobemide was successfully synthesized using this methodology to demonstrate its practical utility.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jakkula Ramarao, Sanjay Yadav, Killari Satyam, Surisetti Suresh
Summary: In this study, we present a novel method for converting imines to amides using an eco-friendly approach. The method involves an NHC-catalyzed oxidation of unactivated aldimines and utilizes molecular oxygen and dimethyl carbonate as the sole oxidant and solvent, respectively, under mild reaction conditions. The developed method demonstrates a broad substrate scope, high yields, and scalability, making it practical for large-scale synthesis.
Article
Chemistry, Multidisciplinary
Le Dung Pham, Red O. Smith-Sweetser, Briana Krupinsky, Carolyn E. Dewey, Jessica R. Lamb
Summary: This study demonstrates that NHC-CDI adducts can be used as masked precursors for switchable organocatalysis, and the CDI substituents can control the reaction profile without changing the NHC structure. By controlling the electronic variations and perturbations on the CDI, the catalytically active temperature and catalyst release range can be controlled.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Yunquan Man, Xiaojun Zeng, Bo Xu
Summary: We have developed an efficient N-heterocyclic carbene (NHC)-catalyzed thioesterification of aldehydes using N-thiosuccinimides as the thiolation reagent. This method allows easy access to highly functionalized thioesters and demonstrates good chemical yields and functional group tolerance.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Applied
Bence S. Nagy, C. Oliver Kappe, Sandor B. otvos
Summary: This study developed a flow chemistry-based process for the oxidation of aldehydes, which enhances process safety by minimizing peracid accumulation. Carboxylic acid formation can be chemically intensified and scalable even in the reactions of deactivated substrates under continuous flow conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Physical
Zhen Li, Meirong Huang, Xinhao Zhang, Jiean Chen, Yong Huang
Summary: This study reports an organocatalytic four-component relay radical coupling to access a broad spectrum of beta-tertiary-gamma-quaternary carboxylic acid derivatives, overcoming the synthetic bottleneck of introducing sterically demanding side chains. The high site control achieved using a triazolium N-heterocyclic carbene catalyst and a transient acyl trapping strategy allows for the preparation of diversified carboxylic acid derivatives in a single pot.
Review
Chemistry, Multidisciplinary
Simon Stenkvist, Sara Bacaicoa, Ellymay Goossens, Henrik Sunden
Summary: The use of oxidative N-heterocyclic carbene (NHC) catalysis has gained significant interest due to the ease of transforming simple starting materials into highly functionalized products. However, the use of stoichiometric amounts of high molecular weight oxidants usually generates equivalent amounts of waste. To address this issue, the use of oxygen as the terminal oxidant in NHC catalysis has been developed. This review covers the development of aerobic oxidative carbene catalysis, including NHC-catalyzed reactions with oxygen, strategies for oxygen activation, and selectivity issues under aerobic conditions.
Review
Chemistry, Multidisciplinary
Kun-Quan Chen, He Sheng, Qiang Liu, Pan-Lin Shao, Xiang-Yu Chen
Summary: In recent years, NHC-catalyzed radical reactions have been gaining attention for their potential to create new activation modes previously inaccessible. Further research and understanding of this emerging area is warranted to explore its synthetic techniques and advantages.
SCIENCE CHINA-CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Tingting Li, Zhichao Jin, Yonggui Robin Chi
Summary: This review discusses N-heterocyclic carbene-catalyzed reactions for the formation of aromatic compounds, categorizing them into 4 types based on activation modes. The achievements, challenges, and future research directions in NHC-catalyzed arene construction processes are summarized. The outlook is based on the authors' opinions and knowledge on the trends of NHC organocatalysis development.
SCIENCE CHINA-CHEMISTRY
(2022)
Article
Chemistry, Organic
Yunquan Man, Shiwen Liu, Bo Xu, Xiaojun Zeng
Summary: A method of N-fluorocarboxamide-directed N-heterocyclic-carbene (NHC)-catalyzed benzylic C-H acylation with aldehydes via the hydrogen atom transfer strategy is disclosed. This method involves a sequence of single-electron transfer, 1,5-hydrogen atom transfer, and radical cross-coupling steps, providing facile access to various highly functionalized ketones with good chemical yields and functional group tolerance.
Article
Chemistry, Organic
Min Zhang, Xinghua Wang, Tingting Yang, Yan Qiao, Donghui Wei
Summary: Identifying the special role of N-heterocyclic carbene (NHC) in organocatalysis remains a major challenge. The study proposed a theoretical model for NHC-catalyzed decarboxylation reactions and found that C-H⋯O hydrogen bond interactions significantly contribute to controlling stereoselectivity in these reactions.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Inorganic & Nuclear
Abdollah Neshat, Rahimeh Khezri, Mohammad Reza Yousefshahi, Mohammad Gholinejad, Fahimeh Varmaghani
Summary: The synthesis and characterization of Nickel(II) complexes with novel pincer-type N-heterocyclic carbene complexes were investigated. The complexes showed high activity as catalysts for the coupling reactions of aryl and alkyl halides. By adjusting the steric hindrance of the ligand, better catalytic performance could be achieved. Under the experimental conditions, a catalyst loading as low as 5 mol% could yield high-productivity products.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Lei Dai, Song Ye
Summary: N-heterocyclic carbene (NHC)-catalyzed reactions involving two-electron and radical pathways have been well-established, with the former more developed than the latter in terms of reaction types and enantioselectivity. In the past decade, several elegant NHC-catalyzed radical reactions have been developed, including oxidation of aldehydes, reductive coupling reactions, and reactions via radical homoenolates.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Organic
Huiping Yin, Tianjiao Huang, Bai Shi, Wei Cao, Chenxia Yu, Tuanjie Li, Kai Zhang, Changsheng Yao
Summary: A practical, convenient, and facile method for constructing highly functionalized 2-pyrrolidinone has been developed using N-heterocyclic carbene (NHC)-catalyzed radical tandem cyclization (30 examples, up to 94% yield). The method is transition metal-free and exhibits broad substrate scope, excellent functional group compatibility, and high efficiency.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Killari Satyam, Jakkula Ramarao, Surisetti Suresh
Summary: The NHC-catalyzed intramolecular benzoin condensation-oxidation allows for the expedient synthesis of diverse cyclic 1,2-diketones incorporated in dibenzo-fused seven-membered heterocycles in good to excellent yields under ambient conditions. The transformation appears to proceed through the benzoin intermediate followed by aerobic oxidation.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Yudai Tanaka, Ryoji Iwamoto, Ryo Sakata, Takahiro Soeta, Kohei Endo, Shuhei Fujinami, Katsuhiko Inomata, Yutaka Ukaji
Article
Chemistry, Multidisciplinary
Takahiro Soeta, Yutaka Ukaji
Article
Chemistry, Multidisciplinary
Mari Yoshida, Naotaro Sassa, Tomomitsu Kato, Shuhei Fujinami, Takahiro Soeta, Katsuhiko Inomata, Yutaka Ukaji
CHEMISTRY-A EUROPEAN JOURNAL
(2014)
Article
Chemistry, Multidisciplinary
Takahiro Soeta, Tomohiro Ishizaka, Yuta Tabatake, Yutaka Ukaji
CHEMISTRY-A EUROPEAN JOURNAL
(2014)
Article
Chemistry, Multidisciplinary
Takahiro Soeta, Syunsuke Matsuzaki, Yutaka Ukaji
CHEMISTRY-A EUROPEAN JOURNAL
(2014)
Article
Chemistry, Multidisciplinary
Yoshiaki Miyamoto, Norihiro Wada, Takahiro Soeta, Shuhei Fujinami, Katsuhiko Inomata, Yutaka Ukaji
CHEMISTRY-AN ASIAN JOURNAL
(2013)
Article
Chemistry, Organic
Takeo Nakano, Takahiro Soeta, Kohei Endo, Katsuhiko Inomata, Yutaka Ukaji
JOURNAL OF ORGANIC CHEMISTRY
(2013)
Article
Chemistry, Organic
Takahiro Soeta, Kaname Tamura, Shuhei Fujinami, Yutaka Ukaji
ORGANIC & BIOMOLECULAR CHEMISTRY
(2013)
Article
Chemistry, Organic
Takahiro Sakai, Takahiro Soeta, Kohei Endo, Shuhei Fujinami, Yutaka Ukaji
Article
Chemistry, Organic
Takahiro Soeta, Takahiro Ohgai, Takahiro Sakai, Shuhei Fujinami, Yutaka Ukaji
Article
Chemistry, Organic
Takahiro Soeta, Yuhta Tabatake, Katsuhiko Inomata, Yutaka Ukaji
Article
Chemistry, Organic
Takahiro Soeta, Kaname Tamura, Yutaka Ukaji
Article
Chemistry, Organic
Takahiro Soeta, Yoshiaki Miyamoto, Shuhei Fujinami, Yutaka Ukaji
Article
Chemistry, Organic
Yutaka Ukaji, Takahiro Soeta
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
(2015)