Review
Chemistry, Multidisciplinary
Wooseok Lee, Inyoung Park, Sungwoo Hong
Summary: Bifunctional reagents that can serve as dual coupling partners have become important tools in organic chemistry for efficient and sustainable synthesis. In particular, bifunctional reagents containing N-heteroaryl groups have attracted attention for their ability to introduce valuable N-heteroaryl moieties into complex molecules. These reagents have been successfully used in visible-light-mediated reactions to achieve difunctionalization of alkenes, alkynes, and [1.1.1]propellanes, providing access to highly functionalized N-heteroarenes. This review summarizes the recent advancements and applications of these bifunctional reagents in photoinduced difunctionalization, highlighting their potential as powerful synthetic tools.
SCIENCE CHINA-CHEMISTRY
(2023)
Article
Chemistry, Organic
Somraj Guha, Imran Kazi, Dhamodharan Sathish, Govindasamy Sekar
Summary: The development of direct and controlled oxidation of C(sp3)-H bonds is of great importance. A metal-free catalytic system utilizing iodine as a catalyst and dimethyl sulfoxide as an oxygen source selectively oxidizes (aryl)(heteroaryl)methanes to (aryl)(heteroaryl)methanols, providing therapeutically important derivatives in good yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Jesse H. Hsu, Tyler E. Ball, Sewon Oh, Erin E. Stache, Brett P. Fors
Summary: This study demonstrates a method to degrade polymers using electrochemistry, and investigates the selectivity and efficiency of the process. Electrocatalytic degradation of polymers with activated C-H bonds is achieved through oxidative polymer degradation promoted by molecular oxygen and electrochemically mediated hydrogen atom transfer (HAT).
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Biochemistry & Molecular Biology
Yue Li, Pengzhen Zhong, Junna Zhao, Zexi Pan, Chen Zhang, Dongmei Cui
Summary: In this study, a selective approach for synthesizing N-([1,3,5]triazine-2-yl) a-ketoamides and N-([1,3,5]triazine-2-yl) amides from ketones with 2-amino[1,3,5]triazines through oxidation and oxidative C-C bond cleavage reaction was reported. The transformation proceeds under mild conditions, provides good functional group tolerance and chemoselectivity, and will serve as a valuable tool for the synthesis of bioactive products.
Article
Chemistry, Multidisciplinary
Wangxi Liu, Yuanqi Wang, Huiting Huang, Jun Wang, Gaoxiang He, Jianyong Feng, Tao Yu, Zhaosheng Li, Zhigang Zou
Summary: Light-driven primary amine oxidation to imines integrated with H2 production presents a promising means to simultaneous production of high-value-added fine chemicals and clean fuels. A spatial decoupling strategy is proposed to overcome the limitations of poor charge separation and uncontrolled hydrogenation. The CoP@ZnIn2S4 photocatalyst exhibits directional and ultrafast carrier separation, leading to significantly higher production rate and selectivity for the photoconversion of benzylamine to N-benzylbenzaldimine.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Ketan S. Mandrekar, Santosh G. Tilve
Summary: The oxidative cleavage of the C-N bond of aryl and heteroaryl (dimethylamino)methyl groups is achieved using molecular iodine as a mild oxidizing agent under ambient conditions in the presence of a mild base. The method can be extended for the synthesis of aryl and other heteroaryl aldehydes and ketones, and has been successfully demonstrated on a gram scale.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Disni Gunasekera, Jyoti P. Mahajan, Yanick Wanzi, Sachini Rodrigo, Wei Liu, Ting Tan, Long Luo
Summary: Here, a unique electrosynthetic method is reported, which selectively oxidizes tertiary amines to generate alpha-amino radical intermediates instead of iminium cations, providing arylation products. An electrochemical descriptor obtained from cyclic voltammetry studies predicts the optimal alternating current (AC) frequency for various amine substrates, avoiding time-consuming trial-and-error methods for optimizing reaction conditions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Inorganic & Nuclear
Huafeng Li, Wenjing Chen, Zelong Yuan, Yuzhen Jin, Yujie Zhao, Pengtao Ma, Jingyang Niu, Jingping Wang
Summary: Three Ru-induced structural interconversion polyoxometalates were synthesized and characterized. The catalytic performances of these compounds in oxidative coupling reactions were found to be strongly dependent on the element contents of the active sites. Compound 1 showed highly efficient photocatalysis, compound 2 exhibited relatively poor efficiency, and compound 3 had no significant contribution to the coupling reaction.
INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Qiangwen Fan, Longwei Zhu, Xuhuai Li, Huijun Ren, Haibo Zhu, Guorong Wu, Jianhua Ding
Summary: In this study, a facile protocol for the photocatalytic oxidation of amines and sulfides to their corresponding imines and sulfoxides using CsPbBr3 as a visible-light catalyst was reported. The results showed excellent yields and selectivity, with different final products depending on the electron-donating or electron-withdrawing groups present in the amines. The reaction mechanism studies revealed the involvement of photogenerated holes, superoxide radicals, singlet oxygen, and free radicals generated by amines in the transformation process.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Bowen Li, Bangke Luo, He Yang, Wenjun Tang
Summary: This study reports an efficient palladium-catalyzed Heck reaction for the synthesis of heterocycles with α-heteroaryl substitution. The method exhibits a broad substrate scope and excellent functional group compatibility. The use of a sterically bulky ligand containing an anthryl moiety is crucial for this transformation. Additionally, an asymmetric variant of the Heck reaction has been achieved, enabling the efficient asymmetric synthesis of (S)-nicotine and its analogues via a cationic palladium pathway.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Korkit Korvorapun, Yannick T. Boni, Thomas C. Maier, Armin Bauer, Thomas Licher, John E. Macor, Volker Derdau, Huw M. L. Davies
Summary: Rhodium-catalyzed C-H insertion by donor/acceptor carbenes is a useful transformation in organic synthesis, but the site-selectivity of the C-H transformation on the target molecule is often a major issue. Chiral rhodium carbene intermediates can achieve site-selective C-H functionalizations of challenging substrates such as N-aryl and N-heteroaryl piperidines, leading to the formation of highly stereoselective C-2 products. Additionally, N-aryl morpholines and piperazines can selectively react at the alpha position to the N-aryl group.
Article
Chemistry, Organic
Xiuju Cai, Xiaoyu Zhou, Ming Huang
Summary: Selective mono-N-methylation of amines with methanol remains challenging, especially for aliphatic amines. In this study, a series of N-heterocyclic carbene (NHC)-amine Ru complexes were developed for this transformation. The Ru4 complex with an NHC-aniline ligand displayed the highest activity and excellent tolerance towards various substrates and sensitive groups.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Analytical
Yuan Liu, Gongyu Li, Ting-Jia Gu, Lingjun Li
Summary: Primary amine-containing metabolites are important in the study of cancers and psychogenic diseases, but their direct detection and visualization from biological systems face challenges. Researchers have developed a simple and efficient strategy, nanosecond photochemical reaction-enabled fast chemical derivatization, for the direct mass spectrometry analysis of these metabolites, with enhanced detection sensitivity.
ANALYTICAL CHEMISTRY
(2022)
Article
Multidisciplinary Sciences
Siyao Wang, Qingqing Zhou, Xiaoping Chen, Rong-Hua Luo, Yunxue Li, Xinliang Liu, Liu-Meng Yang, Yong-Tang Zheng, Ping Wang
Summary: The study presents a convenient strategy for protein modification via a biomimetic quinone-mediated oxidation at the N-terminus, highlighting an efficient and complementary approach to existing strategies for N-terminal modification of proteins. The selective and fast method for N-terminal modification of proteins based on quinone-mediated oxidation of the alpha-amine to aldehyde or ketone is applied to diverse proteins.
NATURE COMMUNICATIONS
(2021)
Article
Engineering, Chemical
Dubing Xu, Rui Zhu, Delong Xie, Yuhui Xie, Hua Wu, Yi Mei
Summary: Researchers proposed grafting organic amines to the chains of resins used in coatings to remove formaldehyde from construction materials, successfully preparing DA-PMA resin films that can effectively eliminate formaldehyde. The smoothness and thermal stability of DA-PMA films are comparable to pure PMA, demonstrating the potential for improved indoor air quality.
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
(2021)
