Article
Chemistry, Multidisciplinary
Chaohuang Chen, Constantin G. Daniliuc, Gerald Kehr, Gerhard Erker
Summary: Deprotonation of [(NHC)(Fmes)B-allyl](+) borenium cations provides access to NHC-stabilized 1-bora-1,3-butadienes, which undergo various organic transformations and serve as precursors for metal complexes.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
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, Inorganic & Nuclear
Karim Azouzi, Lucie Pedussaut, Romane Pointis, Anna Bonfiglio, Riddhi Kumari Riddhi, Carine Duhayon, Stephanie Bastin, Jean-Baptiste Sortais
Summary: Manganese, an earth-abundant transition metal, shows great potential as a catalyst for reduction-type reactions. In this study, a simple bis-N-heterocyclic ligand without phosphine associated with manganese complex [Mn(bis-NHCMes)(CO)(3)Br] was found to effectively catalyze the hydrogenation of carboxylic esters in the presence of KBHEt(3) as an activator at high temperature and pressure.
Article
Chemistry, Multidisciplinary
Jianwen Li, Sheng Tao, Fei Chen, Min Li, Ning Liu
Summary: A variety of zero-valent molybdenum complexes and divalent molybdenum complexes with N-heterocyclic carbenes (NHC)-pyridine ligands were synthesized and their catalytic activities in the cycloaddition reaction of epoxides and CO2 were studied. The divalent molybdenum complexes showed higher catalytic activity for the synthesis of cyclic carbonates compared to the zero-valent molybdenum complexes. The divalent molybdenum complexes combined with TBAI effectively transformed various terminal and internal epoxides under specific conditions.
JOURNAL OF CO2 UTILIZATION
(2023)
Article
Chemistry, Organic
Xiao-Guang Yang, Jun-Jie Li, Feng-Huan Du, Yu-Xin Cheng, Chi Zhang
Summary: In this study, a method for dehydroxytrifluoromethylthiolation of alcohols using a combination of hypervalent iodine(III) reagent TFTI and N-heterocyclic carbenes is reported. This method exhibits excellent stereospecificity and chemoselectivity, resulting in clean inversion of the configuration of hydroxyl groups. It can also be utilized for late-stage modification of structurally complex alcohols.
Article
Chemistry, Organic
Yuxing Cai, Jiean Chen, Yong Huang
Summary: This report describes a successful organocatalytic 1,4-alkylacylation of 1,3-enynes using a ketyl radical generated from single-electron oxidation of the Breslow intermediate as a coupling partner of allenyl radicals. The transformation exhibited remarkable tolerance to both aromatic and radical precursors.
Article
Chemistry, Organic
Hao Liu, Hongwei Zhou, Xingkuan Chen, Jianfeng Xu
Summary: A new method for the enantioselective monoesterification of silicon-centered dialdehydes with alcohols or phenols has been developed using N-heterocyclic carbene (NHC) catalyst, which provides optically active organosilanes with a stereogenic center at the silicon atom. This desymmetrization protocol is suitable for scale-up synthesis and late-stage modifications of complex molecules, and the products can be further transformed to other enantiopure functionalized silanes.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Jiaming Liu, Ming Chen
Summary: A Rhenium-catalyzed stereoselective transposition of allylic alcohols is described. In the presence of 1 mol% of Re2O7, (E)- or (Z)-δ-hydroxymethyl-anti-homoallylic alcohols were converted into the acetals of 2-methyl-1,3-syn-diols with excellent diastereoselectivities. 1,3-syn-Diol acetals can also be synthesized from (E)-δ-hydroxymethyl-syn-homoallylic alcohols.
Article
Chemistry, Organic
Jia Wu, Xiangyun Xu, Chongwen Duan, Shan Chen, Dan Wang, Likui Fang, Weiyang Tang, Fusheng Li
Summary: This article presents a comprehensive account of the regio- and diastereoselective radical multicomponent 1,2-dialkylation of 1,3-enynes via photoexcited Hantzsch ester and chromium co-catalysis to obtain valuable homopropargylic alcohols.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Xin Li, Yan-Yan Ren, Can Chen, Li-Ying Sun, Ying-Feng Han
Summary: This study successfully synthesized and structurally characterized the highly reactive intermediate (Breslow enolate) of NHC-catalyzed radical reactions, and demonstrated the beneficial role of IPr(BIAN) in stabilizing Breslow enolates and ketyl radicals.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Caria Evans, William J. Berkey, Christopher W. Jones, Stefan France
Summary: A Zr-catalyzed synthesis of tetrasubstituted 1,3-diacylpyrroles has been reported using N-acyl alpha-aminoaldehydes and 1,3-dicarbonyl compounds. The reaction showed high yields (up to 88%) and the products were found to be hydrolytically and configurationally stable. The N-acyl alpha-aminoaldehydes were easily prepared from corresponding alpha-amino acids. The reaction could accommodate various substrate types and a range of 1,3-dicarbonyls, including aldehyde derived from a l,l-dipeptide, an in situ generated aldehyde, and an N-acylated glucosamine.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Engineering, Chemical
Feng Bai-cheng, Xi Bao-hu, Zhang Zhen-chao, Hou Yu-hui, Jin Yan, Yao Qing-lin
Summary: This study prepared Ni-Mo/ZrO2 catalysts by a sol-gel method and achieved good catalytic performance in the reductive amination of heterocyclic aldehydes. The Ni-Mo/ZrO2 catalysts with a Ni:Mo ratio of 2:1 exhibited the best results.
CHEMICAL ENGINEERING & TECHNOLOGY
(2022)
Review
Biochemistry & Molecular Biology
Ignacio E. Tobal, Rocio Bautista, David Diez, Narciso M. Garrido, Pilar Garcia-Garcia
Summary: Building blocks play a crucial role in synthetic organic chemistry, with the Diels-Alder cycloaddition reaction being a common application. Cyclic dienes are important for facilitating this reaction. By utilizing cyclic dienes with unique characteristics, biologically active compounds with interesting properties can be synthesized.
Article
Chemistry, Multidisciplinary
Tongfei Zhang, Zhenbo Gao
Summary: This study presents a copper-catalyzed method for the synthesis of thioketals containing CF3 groups from enones and various mercaptans. The results demonstrate the successful preparation of 24 thioketal molecules with moderate to excellent yields, including a preparative scale experiment yielding over 95%. This work enables the straightforward formation of thioketals with CF3 groups and unsaturated double bonds.
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, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
