Article
Chemistry, Physical
Sanjit K. Mahato, Nozomi Ohara, Shrikant M. Khake, Naoto Chatani
Summary: The Ir(III)-catalyzed direct alpha-C-H amidation of imidazole-masked aliphatic carboxylic acids with dioxazolones was successfully achieved, with the key role of the imidazole moiety as a directing group. The products can be easily converted to esters and amides, and the reaction demonstrated a broad substrate scope. Investigating the reaction mechanism led to the proposal of an iridium nitrene intermediate.
Article
Chemistry, Multidisciplinary
Jinhong Chen, Hao Wang, Craig S. Day, Ruben Martin
Summary: A nickel-catalyzed site-selective intermolecular amidation of saturated C(sp(3))-H bonds has been reported, allowing for the introduction of amide functionalities at specific sites. This method exhibits a predictable reactivity pattern, offering a complementary reactivity profile to existing oxidative processes or metal-catalyzed C(sp(3))-N bond-forming reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Yan Du, Xiaoqiang Yu, Jing-Jing Tang, Yang Li, Jiangli Fan, Fei Li, Ming Bao
Summary: This study described a visible-light-driven Mn-catalyzed C(sp(3))-Hamidation of diphenylmethane derivatives with dioxazolones. These reactions occur without the need for an external photosensitizer and achieved satisfactory to good yields (up to 81%) under mild conditions. Mechanistic investigations revealed that the reaction proceeds through a Mn-acyl nitrene intermediate and H-atom abstraction is the rate-determining step. Computational studies showed that the decarboxylation of dioxazolone depends on the conversion of ground-state dioxazolone-bounding Mn species to quartet spin state via visible-light irradiation.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Raj K. Tak, Hidetoshi Noda, Masakatsu Shibasaki
Summary: This study reports a copper-catalyzed intramolecular asymmetric electrophilic amination of aromatic rings, using isoxazolidin-5-ones to generate copper-alkyl nitrene. Copper catalysis promotes three classes of asymmetric transformations, providing various cyclic and linear beta-amino acids in their enantioenriched forms.
Review
Chemistry, Multidisciplinary
Seung Youn Hong, Yeongyu Hwang, Minhan Lee, Sukbok Chang
Summary: Catalytic reactions constructing carbon-nitrogen bonds are important in synthetic and medicinal chemistry due to the prevalence of nitrogen-containing motifs in natural products and drugs. C-H amination offers a more efficient approach by directly converting C-H bonds into C-N bonds, bypassing the need for prefunctionalized substrates. The development of novel catalytic platforms utilizing metal-nitrenoids has expanded the scope of C-N bond-forming reactions and enabled the synthesis of diverse compounds.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Article
Chemistry, Multidisciplinary
Jing-Jing Tang, Ning Yan, Yiwei Zhang, Yi Wang, Ming Bao, Xiaoqiang Yu
Summary: An efficient visible-light-induced iron-catalyzed S-N coupling of thiols with dioxazolones under mild conditions has been developed. The reaction occurs without the need for ligands and photosensitizers, showing satisfactory yields, broad functional group tolerance, and an easy operation procedure. Preliminary mechanistic investigations suggest that the reactions proceed via a radical pathway.
Article
Chemistry, Multidisciplinary
Hillol Khatua, Subrata Das, Sima Patra, Sandip Kumar Das, Satyajit Roy, Buddhadeb Chattopadhyay
Summary: A catalytic system for intermolecular benzylic C(sp3)-H amination utilizing 1,2,3,4-tetrazole as a nitrene precursor via iron catalysis has been developed. This method enables direct installation of 2-aminopyridine into the benzylic and heterobenzylic position, selectively aminating 2 degrees benzylic C(sp3)-H bond over the 3 degrees and 1 degrees benzylic C(sp3)-H bonds. The experimental studies reveal that the C(sp3)-H amination proceeds via the formation of a benzylic radical intermediate.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Zuo Zuo Wu, Tapas Adak, Martin C. Dietl, Tao Wang, Chao Hu, Hongwei Shi, Petra Kraemer, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi
Summary: The study presents a novel gold-catalyzed 2-fold reaction of a bromoalkyne with anthranils to produce alpha-ketoamides. This method provides a new synthetic approach for preparing this functional group.
Review
Chemistry, Applied
Sereena Sunny, Ramasamy Karvembu
Summary: C-N bond formation reactions have gained significant interest recently due to the prevalence of nitrogen-containing compounds in pharmaceuticals. The use of directing-group-assisted C-H amidation with cobalt as a catalyst has been a focus for its unique properties and efficiency in selective amidation of C-H bonds. The evolution of directing group preferences and their function in site selection have been discussed in recent developments of this field.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Gong Chen, Kenta Arai, Kazuhiro Morisaki, Takeo Kawabata, Yoshihiro Ueda
Summary: A method for selective C(sp(3))-H amidation of N,N-dimethylanilines was developed, exclusively targeting the N-methyl group for amidation while leaving the C(sp(2))H bonds on the aromatic ring untouched.
Article
Chemistry, Physical
Yanjun Wan, Emmanuel Ramirez, Ayzia Ford, Vanessa Bustamante, Gang Li
Summary: The study presents an iron-catalyzed method for accessing gamma-functionalized amides through C-H functionalization, involving the formation of an iron nitrenoid species and a specific mechanism. It demonstrates broad substrate compatibility and practicality, with the catalyst showing high turnovers on complex natural products.
Article
Chemistry, Organic
He Zhang, Meng-Chan Sun, Li-Ming Yin, Donghui Wei, Mao-Ping Song, Dandan Yang, Jun-Long Niu
Summary: This study presents an efficient metal-free intramolecular C(sp(3))-H bond sulfonamidation reaction, offering a new synthetic approach to 5-membered cyclic sulfonamides. The reaction mechanism involves proton transfer coupled with the S(N)2 (PTS(N)2) process, distinguishing it from other pathways.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Ethan Zars, Lisa Pick, Abinash Swain, Mrinal Bhunia, Patrick J. Carroll, Dominik Munz, Karsten Meyer, Daniel J. Mindiola
Summary: In this study, a base metal complex was used as a catalyst for the intermolecular amination reaction of Csp3-H bonds. The reaction exhibited high selectivity and good substrate tolerance.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Xiao Rui Wen, Wen Qing Zhu, Cai Lin Zhang, Hong Li, Jin Zhang, Min Ge Yang, Yong Li Kou, Yu Xia Liu, Yang Li
Summary: Amide compounds are important in various fields like biomedical chemistry, materials science, and life science. The synthesis of alpha-CF3 amides, especially compounds with 3-(trifluoromethyl)-1,3,4,5-tetrahydro-2H-benzo[b][1,4]diazepine-2-one, has been a challenge due to their tensile properties and instability of the rings. However, by using a palladium-catalyzed carbonylation reaction, we have successfully synthesized alpha-CF3 acrylamide. By controlling the ligands, we can obtain different amide compounds with good substrate adaptability and functional group tolerance.
Review
Chemistry, Organic
Ming Zhang, Shengliang Zhong, Yiyuan Peng, Jianwen Jiang, Yongli Zhao, Changfeng Wan, Zhenming Zhang, Rongli Zhang, Ai Qin Zhang
Summary: This review discusses the palladium-catalyzed sp(3) C-H activation/functionalization of amino acids and peptides, including intermolecular and intramolecular functionalization methods.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Multidisciplinary Sciences
Lulu Wang, Kuo-Wei Huang, Jitao Chen, Junrong Zheng
Article
Chemistry, Physical
Gang-Hua Deng, Yuneng Shen, Hailong Chen, Yajing Chen, Bo Jiang, Guorong Wu, Xueming Yang, Kaijun Yuan, Junrong Zheng
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2019)
Article
Chemistry, Physical
Can Gao, Xunhua Wang, Jitian Liu, Xiaoxun Li
Summary: This study presents a palladium-catalyzed asymmetric [4 + 4] cycloaddition, allowing for efficient synthesis of highly stereochemically controlled nitrogen-heterocyclic compounds. The method provides good regio-, stereo-, and enantioselectivity, with the ability to tolerate complex substrates derived from natural products.
Article
Chemistry, Physical
Jianxin Guan, Chengzhen Shen, Jie Peng, Junrong Zheng
Summary: Aggregation-induced emission (AIE) refers to the stronger emission of molecules in the aggregate state compared to the solution state, driven by factors such as fast energy dissipation and weak intermolecular coupling. The key to AIE lies in controlling molecules to cross or not to cross a conical intersection (CI) by changing the phase of molecules, thereby tuning the luminescence efficiency. Manipulating the formation of CIs can also be an alternative way to modulate luminescence efficiency.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2021)
Article
Chemistry, Physical
Qirong Yang, Jianxin Guan, Jingwen Deng, Zihan Xu, Zhihao Yu, Junrong Zheng
Summary: Research has been conducted on an unconventional heterojunction device based on a graphene-MoSe2 hybrid interface, which contains only two atomic layers and shows a significant photoelectric response aided by electron transfers from MoSe2 to graphene. The two-layered architecture simplifies the fabrication of optoelectronic devices and eliminates damage-prone transfer processes.
JOURNAL OF CHEMICAL PHYSICS
(2022)
Article
Chemistry, Physical
Zhuowei Hou, Jianxin Guan, Jie Peng, Xinmao Li, Zhihao Yu, Junrong Zheng
Summary: Conical intersections (CIs) play a crucial role in the nonradiative decay of electronically excited states. This study investigates double CIs in tetraphenyl ethylene using ultrafast spectroscopy and fluorescence. The results reveal the relationship between fluorescence quantum yield, cyclization efficiency, and excitation wavelength.
JOURNAL OF CHEMICAL PHYSICS
(2022)
Article
Chemistry, Physical
Xinmao Li, Jianxin Guan, Chengzhen Shen, Zhihao Yu, Junrong Zheng
Summary: The aggregation morphologies of conjugated polymers in solutions and solid films are important for their optoelectronic applications. It remains a great challenge to determine their conformations in either liquids or solids due to the amorphous state of the polymers. This study applied a ps/fs synchronized 2D IR technique to investigate the molecular conformations of a high-mobility n-type low-bandgap copolymer, N2200, dissolved in CHCl3 and CCl4, and in solid films cast from both solutions. The results provide insights into the balance and competition between the polymer/polymer interaction and the polymer/solvent interaction in determining the morphology of solid films cast from solution.
JOURNAL OF CHEMICAL PHYSICS
(2023)
Article
Multidisciplinary Sciences
Lulu Wang, Jie Yan, Yuexian Hong, Zhihao Yu, Jitao Chen, Junrong Zheng
Summary: By utilizing the unique ultrafast proton conduction mechanism in vanadium oxide electrodes, a new aqueous battery with high rate capability up to 1000 C and extremely long life of 0.2 million cycles has been developed. The ultrafast kinetics and excellent cyclic stability are achieved through rapid 3D proton transfer in vanadium oxide via a special pair dance switching mechanism. This work provides insight into developing high-power and long-life electrochemical energy storage devices with nonmetal ion transfer through special pair dance top-ochemistry dictated by hydrogen bond.
Article
Chemistry, Physical
Jie Peng, Xin He, Yao Li, Jianxin Guan, Baihua Wu, Xinmao Li, Zhihao Yu, Jian Liu, Junrong Zheng
Summary: Understanding the mechanisms of aggregation-induced emission (AIE) is crucial for the design of better AIE-gens. Diphenylethylene (DPE) featured molecules, with their propeller structure, are important AIE-gens. Through ultrafast UV/IR spectroscopy and theoretical calculations, three representative DPE-featured AIE-gens, triphenylethylene, cis-stilbene, and trans-stilbene, were investigated. The results suggest that crossing conical intersections (CIs) with flexible structural evolutions in solutions reduces fluorescence, while crossing CIs is restricted in solids, leading to no fast nonradiative decay competing with spontaneous emission.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2023)
Article
Chemistry, Organic
Xunhua Wang, Jianfeng Yang, Ruifeng Lv, Pengfei Song, Denghui Ye, Jitian Liu, Xiaoxun Li
Summary: This study discloses a palladium-catalyzed cycloaddition strategy that achieves high selectivity and yield. The method is capable of constructing complex molecules with specific stereostructures, and the products can be further transformed into other chiral compounds.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Can Gao, Ting Zhang, Xiaoxun Li, Jing-De Wu, Jitian Liu
Summary: A new asymmetric reaction strategy for the synthesis of enantiomerically enriched and polycyclic molecules has been reported. By using a newly designed catalyst, high yields and high selectivities were achieved. This method offers mild reaction conditions and good functional group tolerance, making it important for the synthesis of organic compounds.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Physical
Chao Hou, Jingwen Deng, Jianxin Guan, Qirong Yang, Zhihao Yu, Yilin Lu, Zihan Xu, Zefan Yao, Junrong Zheng
Summary: The research reveals that laser irradiation can enhance the photoluminescence of monolayer MoS2, with different effects observed under different atmospheres, being more significant in the presence of oxygen. Additionally, physically adsorbed water also plays a role in enhancing the photoluminescence of monolayer MoS2.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2021)
Article
Chemistry, Physical
Jiebo Li, Yufan Zhang, Junrong Zheng
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2019)
