Article
Chemistry, Multidisciplinary
En Li, Jiean Chen, Yong Huang
Summary: The Michael reaction is an important method for preparing functional molecules with a β-stereogenic center. However, the enantioselective seleno-Michael addition is still poorly explored. In this study, a highly enantioselective Michael addition reaction of alkyl selenols to enones was reported, introducing a Se atom asymmetrically to an electron-deficient double bond. A chiral bifunctional N-heterocyclic carbene (NHC)/thiourea catalyst was developed and showed remarkable selectivity in delivering chiral β-seleno ketones.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Shuting Tan, Jian-Guo Liu, Ming-Hua Xu
Summary: A rhodium-catalyzed asymmetric 1,4-addition reaction provides a practical approach for synthesizing highly enantioenriched chiral N-alkylindoles.
Article
Chemistry, Multidisciplinary
Zeyu Han, Derek P. Gates
Summary: This study discovered a high-yielding P=C bond metathesis of phosphaalkenes catalyzed by N-heterocyclic carbenes, resulting in cyclic oligomers formally derived from ArP=PAr. Preliminary mechanistic studies revealed NHC=PAr as key phosphinidene transfer agents, and novel cyclic intermediates were observed. This work represents a rare application of non-metal-based catalysts for transformations involving main-group elements.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Review
Chemistry, Physical
Guangjin Zhen, Kai Jiang, Biaolin Yin
Summary: Dearomative reactions enable the concise assembly of highly functionalized three-dimensional molecules by disrupting the aromaticity of starting materials. N-heterocyclic carbenes (NHCs) have emerged as powerful catalysts for dearomatization reactions, allowing for the construction of natural product and drug skeletons. This overview summarizes the progress in NHC-catalyzed dearomative reactions, classifying the reactions by modes and categories of intermediates and providing representative mechanisms.
Review
Chemistry, Inorganic & Nuclear
Pengcheng Gao, Michal Szostak
Summary: The catalytic addition of water to unsaturated C-C or C-N p bonds is an important and environmentally sustainable method for forming C-O bonds. Traditional acid-catalyzed hydration requires strong acids or toxic mercury salts, limiting its practical applications and posing safety and environmental concerns. Transition-metal-catalyzed hydration with NHC ligands has gained significant attention and has achieved major progress. This review provides a comprehensive overview of hydration reactions catalyzed by transition metal-NHC complexes and their applications in catalytic hydration.
COORDINATION CHEMISTRY REVIEWS
(2023)
Article
Chemistry, Multidisciplinary
Yingtao Wu, Mingrui Li, Jiaqiong Sun, Guangfan Zheng, Qian Zhang
Summary: In this research, an NHC-catalyzed atroposelective esterification of biaryl dialdehydes is described as a general and practical strategy for the construction of axially chiral aldehydes. The method features excellent enantioselectivity, mild conditions, good functional-group tolerance, and applicability to late-stage functionalization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Chun-Lin Zhang, Yuan-Yuan Gao, Hai-Ying Wang, Bang-An Zhou, Song Ye
Summary: An NHC-catalyzed de novo synthesis method for axially chiral benzothiophene/benzofuran-fused biaryls has been reported, providing a convenient and efficient access to these compounds with high enantioselectivities. The method also works well for the synthesis of tetra-ortho-substituted biaryls, addressing an unsolved problem in the field.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Jin Hyun Park, Sun Bu Lee, Byeong Jun Koo, Han Yong Bae
Summary: A water-accelerated, N-heterocyclic carbene (NHC)-catalyzed aza-Michael addition reaction was reported for the synthesis of beta-aminosulfonyl fluorides, key components of the SuFEx reaction. Water as a reaction medium significantly enhanced the reaction rate and demonstrated late-stage ligation with bioactive molecules.
Article
Chemistry, Multidisciplinary
Meng Yu, Xuefeng Yong, Weiwei Gao, Chun-Yu Ho
Summary: The study successfully achieved diastereodivergent hydrosilylative enyne cyclization using IPrCl catalyst and R3SiH silane, offering high generality and broad scope of products. The method selectively obtained heterocycles containing homoallylsilane, while suppressing competitive reactions effectively.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Applied
Kenya Tamaribuchi, Jiaqi Tian, Kengo Akagawa, Kazuaki Kudo
Summary: Enantioselective Michael addition of beta-dicarbonyl compounds towards nitroalkenes was achieved using an immobilized, N-terminal-guanidinylated peptide catalyst. Various nucleophiles and electrophiles were employed, with the resin-supported catalyst being recyclable for five cycles. This method shows promise for industrial applications.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Polymer Science
Takuhiro Nomura, Makoto Ryukan, Shin-ichi Matsuoka, Masato Suzuki
Summary: Experimental studies revealed that gamma-butyrolactone (γ-BL) undergoes graft co-oligomerization with (meth)acrylates catalyzed by N-heterocyclic carbene (NHC), instead of hybrid co-oligomerization with ester linkage in the main chain, as initially hypothesized.
Article
Polymer Science
Marta Angoy, M. Victoria Jimenez, Fernando J. Lahoz, Eugenio Vispe, Jesus J. Perez-Torrente
Summary: A series of neutral and cationic rhodium complexes with NHC ligands functionalized with different substituents have been prepared and shown to efficiently catalyze the polymerization of phenylacetylene. The catalytic activity of these complexes is influenced by the type of NHC ligand functionalization, with complexes bearing flexible amino-alkyl wingtips showing higher activity. Studies reveal the presence of branched polymers in samples obtained with certain catalysts, indicating the involvement of neutral alkynyl species in the polymerization process.
Article
Chemistry, Multidisciplinary
Tingting Li, Chengli Mou, Puying Qi, Xiaolin Peng, Shichun Jiang, Gefei Hao, Wei Xue, Song Yang, Lin Hao, Yonggui Robin Chi, Zhichao Jin
Summary: A catalytic atroposelective cycloaddition reaction between thioureas and ynals has been developed, enabling the establishment of C-N axial chirality with excellent optical purities. The resulting axially chiral thiazine derivative products contain multiple functional groups and are suitable for further transformations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
He Sheng, Qiang Liu, Bei-Bei Zhang, Zhi-Xiang Wang, Xiang-Yu Chen
Summary: This report presents a study on the blue light-induced N-heterocyclic carbene (NHC)-catalyzed single electron reduction method for the synthesis of biaryl cross-coupling products. It was found that under blue light irradiation, the NHC/tBuOK combination could construct powerful photoactive architectures to promote single electron transfer for the reduction of C-aryl-F bonds, resulting in the formation of highly reducing NHC radical anions. It was also observed that this strategy successfully reduced C-aryl-O, C-aryl-N, and C-aryl-S bonds for biaryl cross-couplings.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Jayeeta Bhattacharjee, Marius Peters, Dirk Bockfeld, Matthias Tamm
Summary: The NHC-phosphinidene adducts reacted with AlMe3 to generate monoaluminum and dialuminum complexes, which were found to act as efficient initiators for ring-opening polymerization of rac-lactide. The monoaluminum complexes produced highly isoselective poly(rac-lactide), while the dialuminum complex resulted in almost atactic polymers, indicating the importance of the coordination-insertion mechanism with carbene-phosphinidene ligands as stereodirecting groups.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Polymer Science
Paige A. Shaw, Maxime Klausen, Mark Bradley
Summary: A light-responsive polymer capable of controlled release of camptothecin and generation of reactive oxygen species (ROS) was developed, which exhibited high cancer cell killing activity through both camptothecin release and ROS generation.
Article
Polymer Science
Donghui Zhang, Shiqi Liu, Zhihao Cai, Weizhe Luo, Guojian Liu, Runhui Liu
Summary: A straightforward and efficient method for synthesizing NPC monomers has been developed in this study, which enhances the availability of NPC monomers and facilitates the synthesis of polypeptides.
