Article
Chemistry, Organic
Chun -Lin Zhang, Hai-Ying Wang, Ying Huang, Xin-Han Wang, Song Ye
Summary: An N-heterocyclic carbene-catalyzed three-component reaction has been developed for the synthesis of multisubstituted benzenes. The reaction demonstrates mild conditions, high efficiency, and chemoselectivity, leading to the formation of pentasubstituted benzenes in good to high yields.
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, 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, Multidisciplinary
En Li, Kai Tang, Zhuhui Ren, Xiaoyun Liao, Qianchen Liu, Yong Huang, Jiean Chen
Summary: The successful enantioselective beta-alkylation of homoenolates using C-sp3 electrophiles through an S(N)2 strategy is reported. The method shows a broad scope and delivers good yields and excellent enantioselectivities (up to 99% ee). It enables the installation of drug-like structural motifs and presents a concise synthetic route to chiral pyrroloindoline-type skeletons. Preliminary mechanistic studies support a direct S(N)2 mechanism.
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, Multidisciplinary
Ashmita Singh, Anudeep Kumar Narula
Summary: A new methodology was developed for the synthesis of substituted, bicyclic 3-benzoyl flavanone derivatives by [4+2] annulations of salicylaldehyde with chalcones using N-heterocyclic carbene (NHC) as a catalyst, I-2 as co-catalyst and tert-butyl hydroperoxide (TBHP) as an oxidant in ethanol. The methodology was effective across a range of electron-deficient to electron-rich substrates.
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
Biochemical Research Methods
Fady Nahra, Nikolaos Tzouras, Alba Collado, Steven P. Nolan
Summary: N-heterocyclic carbene gold(I) chloride and hydroxide complexes are commonly used as synthetic reagents and efficient catalysts. This study describes a straightforward and practical method for synthesizing mononuclear gold complexes with high yields, as well as the synthesis of a mononuclear gold(I) hydroxide complex and an improved synthesis method for a dinuclear gold(I) hydroxide complex. This methodology offers advantages such as the use of sustainable reaction solvents and commercially available starting materials.
Article
Chemistry, Multidisciplinary
Guanjie Wang, Juhui Huang, Linxue Zhang, Jinna Han, Xiaoxiang Zhang, Jie Huang, Zhenqian Fu, Wei Huang
Summary: Axially chiral molecules are widely used in various fields of chemistry, and the synthesis of axially chiral molecules catalyzed by NHCs remains underdeveloped. In this study, we successfully achieved the atroposelective synthesis of axially chiral heteroaryl-aryls using chiral NHCs as catalysts for highly enantioselective Coates-Claisen rearrangements via catalytically generated alpha, beta-unsaturated acyl azoliums. This approach enables the concise synthesis of tetra-ortho-substituted 2-pyrones with good yield and chirality control.
SCIENCE CHINA-CHEMISTRY
(2022)
Article
Chemistry, Organic
Yunpeng Chu, Meng Wu, Fang Hu, Panpan Zhou, Zhengqiang Cao, Xin-Ping Hui
Summary: The first atroposelective synthesis of pyrrolo[3,4-b]pyridines catalyzed by N-heterocyclic carbene has been achieved, leading to a wide range of chiral atropisomers with high yields and excellent enantioselectivities (96-99% enantiomeric excess). Experimental results and density functional theory calculations demonstrate the high thermal stability of the C-N axial chirality in the product.
Article
Chemistry, Organic
Kosuke Yasui, Miharu Kamitani, Hayato Fujimoto, Mamoru Tobisu
Summary: This study reports on the N-heterocyclic carbene (NHC)-catalyzed Truce-Smiles rearrangement of aniline derivatives, where an unactivated C(aryl)-N bond is cleaved to form a new C(aryl)-C bond. The key to the success of this reaction lies in the utilization of highly nucleophilic NFIC, which enables the formation of a highly nucleophilic ylide intermediate generated from an alpha,beta-unsaturated amide.
Article
Chemistry, Organic
Yingxin Ye, Zhongxian Liu, Yazhou Wang, Yin Zhang, Fan Yin, Qi He, Jiahao Peng, Kai Tan, Yuehai Shen
Summary: PEPPSI-type Pd complexes with NHC ligands containing N-(4-indolyl) side chains were synthesized and evaluated for their catalytic activity in three reactions. The results showed that complex 8g, with an unsymmetric N-(3-isopropyl-1,5,7-trimethyl-2-phenylindol-4-yl) NHC, exhibited the highest activity and outperformed Pd-PEPPSI-IPr. This study demonstrates the promising platform of N-(4-indolyl) side chains for the development of synthetically useful NHC ligands.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Chuntao Wang, Dong Zhu, Rui Wu, Shifa Zhu
Summary: This study reports a Rh2(II)-catalyzed asymmetric enyne cycloisomerization for the synthesis of chiral difluoromethylated cyclopropane derivatives, which can be easily transformed into highly functionalized difluoromethylated cyclopropanes with vicinal all-carbon quaternary stereocenters through ozonolysis. Mechanistic studies and X-ray crystallography of alkyne-dirhodium complexes suggest that cooperative weak hydrogen bondings between the substrates and the dirhodium catalyst may be crucial in this reaction.
Article
Chemistry, Multidisciplinary
Daniela M. Carminati, Jonathan Decaens, Samuel Couve-Bonnaire, Philippe Jubault, Rudi Fasan
Summary: An efficient biocatalytic method for high diastereo- and enantioselective synthesis of CHF2-containing trisubstituted cyclopropanes has been developed, showing excellent yield and stereoselectivity. The methodology provides a powerful strategy for the stereoselective synthesis of fluorinated building blocks, as demonstrated by the formal total synthesis of a CHF2 isostere of a TRPV1 inhibitor.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)