Review
Chemistry, Multidisciplinary
Senjie Ma, John F. Hartwig
Summary: Catalytic intermolecular hydroamination of alkenes is a valuable method for the synthesis of amines with important applications in various fields. However, achieving high yield and selectivity is challenging due to the lack of thermodynamic driving force and the occurrence of side reactions. Late transition-metal complexes have shown advantages in catalyzing hydroaminations. This Account describes the progress in catalytic hydroamination reactions catalyzed by late transition-metal complexes, including additions to activated and unactivated alkenes, and the development of enantioselective hydroaminations.
ACCOUNTS OF CHEMICAL RESEARCH
(2023)
Article
Chemistry, Physical
Ruchi Dixit, Himanshu Sharma, Francine Agbossou-Niedercorn, Kumar Vanka, Christophe Michon
Summary: We conducted a theoretical study on silver-dependent enantiodivergent reactions. By applying a specific catalyst and solvent switch, the asymmetric intramolecular hydroamination of alkenes can be achieved, resulting in the formation of both enantiomers of the products.
Article
Engineering, Environmental
Chao Qu, Huiqin Wang, Yi Man, Zhe Li, Peng Ma, Peng Chang, Xin Li, Chunmiao Han, Yudong Pang, Hui Xu
Summary: A feasible strategy of D-A-A structure is proposed to improve the PL and EL performance of red TADF emitters. Four newly designed and synthesized TADF emitters with D-A-A and D-A-D structures are demonstrated. The asymmetric compounds show abundant intra- and inter-molecular C-H···O hydrogen bonds, promoting charge transfer. Additionally, the steric hindrance of DPPO group effectively suppresses concentration quenching, resulting in better PL quantum yields and lower nonradiation rates.
CHEMICAL ENGINEERING JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Physical
Antonella Dentoni Litta, Antonio Buonerba, Alberto Casu, Andrea Falqui, Carmine Capacchione, Antonio Franconetti, Hermenegildo Garcia, Alfonso Grassi
Summary: The synthesis of aromatic ketimines via hydroamination of phenylacetylenes with anilines has been achieved with high yields and excellent selectivity using gold nanoparticles embedded in a copolymer matrix. The nanoporous polystyrenic support played a crucial role in enhancing the catalyst performance. The study also identified a new reaction pathway for the hydroamination reaction involving the formation of AN aggregates stabilized by hydrogen bonding interactions.
JOURNAL OF CATALYSIS
(2021)
Article
Chemistry, Organic
Young Ho Kim, Dong Bin Kim, Su San Jang, So Won Youn
Summary: A Pd-catalyzed intramolecular allylic C-H amination method has been developed, allowing for the synthesis of diverse 1,3-X,N-heterocycles through selective allylic C-H cleavage and pi-allylpalladium formation. The use of substrates containing a labile allylic moiety and new catalytic systems overcomes significant challenges for achieving highly chemo- and regioselective allylic C-H amination.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Julien Dieu, Francois Jerome, Catherine Batiot-Dupeyrat
Summary: Non-thermal atmospheric plasma is capable of cleaving the N-H bond of NH3 to form aminium radicals, which then react with ethylene to produce ethylamine with a yield of 17%. This technology can also be applied to n-octene, leading to the formation of 1-octylamine, demonstrating anti-Markovnikov addition of NH3.
REACTION CHEMISTRY & ENGINEERING
(2021)
Article
Chemistry, Multidisciplinary
Daven Foster, Pengchao Gao, Ziyun Zhang, Gellert Sipos, Alexandre N. Sobolev, Gareth Nealon, Laura Falivene, Luigi Cavallo, Reto Dorta
Summary: Chiral, cationic NHC-iridium complexes have been introduced as catalysts for the intramolecular hydroamination reaction of unactivated aminoalkenes, showing high activity and selectivity. By eliminating a major deactivation pathway, the efficiency of the reaction is improved. Through experimental and computational studies, valuable insights into the reaction mechanism have been gained.
Article
Chemistry, Multidisciplinary
Zhenmei Huang, Bowen Lei, Dezhi Yang, Dongge Ma, Zhengyang Bin, Jingsong You
Summary: The development of a medium ring-lock strategy for TADF emitters has been introduced to enhance the efficiency of OLEDs. The electron-deficient heptagonal diimide lock improves electron-withdrawing ability and increases the photoluminescence quantum yield. This modified intramolecular-lock strategy enables the assembly of high-performance non-doped OLEDs.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Waqar Ahmed, Aiman Sadaf, Pil Seok Chae
Summary: A new method for synthesizing 4,5-unsaturated sulfonamides is presented, using aryl-substituted alkenes, allylic alcohols, and commercially available sulfonamides as starting materials. This method utilizes a catalyst of copper(I)-BF3 and shows good compatibility with different reagents, resulting in reasonably good yields (60-90%).
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Inorganic & Nuclear
Emily Y. Fok, Veronica L. Show, Adam R. Johnson
Summary: The laboratory has developed catalysts based on earth abundant titanium for asymmetric reactions, showing improved enantioselectivity with new ligands, but unexpected dimerization of the catalyst resulted in reduced activity.
Article
Chemistry, Physical
Ricarda Duehren, Peter Kucmierczyk, Ralf Jackstell, Robert Franke, Matthias Beller
Summary: The state-of-the-art catalyst system using palladium complexes for hydroxy- and alkoxycarbonylations of olefins has been complemented by a ruthenium-catalyzed hydroxycarbonylation method. This efficient transformation utilizes an inexpensive Ru-precursor and PCy3 ligand in the presence of hexafluoroisopropanol as solvent and acid co-catalyst to provide various carboxylic acids from unfunctionalized olefins.
CATALYSIS SCIENCE & TECHNOLOGY
(2021)
Article
Chemistry, Multidisciplinary
Steve H. Park, Geunsu Bae, Ahhyeon Choi, Suyeon Shin, Kwangmin Shin, Chang Hyuck Choi, Hyunwoo Kim
Summary: This study presents an electrocatalytic approach for the intramolecular hydroamination of allylic sulfonamides to access azetidines. The combination of cobalt catalysis and electricity enables the regioselective generation of key carbocationic intermediates, which undergo intramolecular C-N bond formation. Mechanistic investigations suggest that catalyst regeneration by nucleophilic cyclization or the second electrochemical oxidation to access the carbocationic intermediate is involved in the rate-determining step (RDS) of the electrochemical protocol.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Engineering, Environmental
Huanhuan Li, Yuzheng Wang, Lan Yu, Chang Liu, Cefeng Zhou, Sibing Sun, Mingguang Li, Ye Tao, Gaozhan Xie, Hui Xu, Wei Huang, Runfeng Chen
Summary: The study successfully designed and synthesized a symmetric V-shaped triazine host DCzT with non-covalent intramolecular interactions, replacing the phenyl core of the twisted blue host mCP. Through the NCIs, DCzT demonstrated a closed plane, boosting ordered molecular packing arrangement for enhanced carrier transport channel performance and achieving efficient white TADF OLEDs.
CHEMICAL ENGINEERING JOURNAL
(2021)
Article
Multidisciplinary Sciences
Yun-Nian Yin, Rui-Qi Ding, Dong-Chen Ouyang, Qing Zhang, Rong Zhu
Summary: The authors have developed a single-step approach for the synthesis of α-tertiary amides via cobalt-catalyzed intermolecular oxidative hydroamidation of unactivated alkenes. This method shows good selectivity for terminal alkenes and avoids competing reactions with other functional groups, providing a straightforward access to a diverse array of hindered amides.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.