Article
Chemistry, Organic
Jie Cao, Daqi Lv, Fei Yu, Mong-Feng Chiou, Yajun Li, Hongli Bao
Summary: The vicinal diamine motif is important in natural products, drug design, and organic synthesis, and developing methods for synthesizing vicinal diamines has long been of interest. This study reports on a regioselective intermolecular three-component vicinal diamination reaction using styrenes, acetonitrile, and azodicarboxylates. The diamination products can be obtained in moderate to excellent yields via the Ritter reaction, and synthetic applications and theoretical studies of this reaction have been conducted.
Article
Chemistry, Organic
Dawid J. Kucharski, Rafal Kowalczyk, Przemyslaw J. Boratynski
Summary: Novel 1,2-diamines based on the mefloquine scaffold were prepared, with the most effective 11-aminomefloquine obtained through conversion of the 11-alcohol and subsequent alkylation. The substitution reactions mostly retained the configuration, and enantiomerically pure products were obtained through resolution. The efficacy evaluation of the obtained vicinal diamines showed that erythro-11-aminomefloquine is a superior catalyst in asymmetric transformations.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Byung Joo Lee, Andrew R. Ickes, Anil K. Gupta, Seth C. Ensign, Tam D. Ho, Anika Tarasewicz, Evan P. Vanable, Gregory D. Kortman, Kami L. Hull
Summary: In this study, the rhodium-catalyzed hydroamination of allyl amine derivatives using various amine nucleophiles was presented. This methodology provides a powerful approach for the synthesis of unsymmetrical vicinal diamines and has been demonstrated to be useful in the rapid synthesis of bioactive molecules and analogs.
Article
Chemistry, Multidisciplinary
Andrea Geraci, Uros Stojiljkovic, Kevin Antien, Nihad Salameh, Olivier Baudoin
Summary: Chiral 1,2-diamines are important structures in bioactive natural products, active pharmaceutical ingredients, ligands for asymmetric catalysis, and organocatalysts. However, constructing chiral 1,2-diamine motifs is still challenging. To address this, researchers developed an iridium(III)-catalyzed intermolecular C(sp3)-H amidation reaction using a new and cleavable exo-protecting/directing group. This method allows for the synthesis of scalemic free 1,2-diamines from easily accessible precursors.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Hui-Jie Pan, Yamei Lin, Taotao Gao, Kai Kiat Lau, Wei Feng, Binmiao Yang, Yu Zhao
Summary: This study presents an unprecedented diastereoconvergent synthesis of vicinal diamines from diols, using an economical and redox-neutral process. Efficient and diastereoselective coupling of readily available anilines and 1,2-diols under cooperative ruthenium and Lewis acid catalysis was achieved, along with the first enantioconvergent double amination of racemic 1,2-diols through an effective chiral iridium/phosphoric acid co-catalyzed procedure, leading to practical access to highly valuable enantioenriched vicinal diamines.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Mingkang Zhou, Yaodong Lin, Xiao-Xuan Chen, Guangqing Xu, Lung Wa Chung, Wenjun Tang
Summary: We report the chiral diboron-templated asymmetric homocoupling of aryl alkyl ketimines, leading to the formation of chiral vicinal tetrasubstituted diamines with high enantioselectivities and good to high yields. This powerful and efficient reaction is achieved by rational design and engineering of chiral diborons, which participate in a [3,3]-sigmatropic rearrangement. DFT studies reveal that different conformational assembling strategies of chiral diborons ensure the excellent enantioselectivity in the tight concerted transition states.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Yongzhuo Xu, Boqiang Wang, Jiajia Wang, Xuan Zhou, Jiaxing Chen, Xinjia Guo, Guo-Jun Deng, Wen Shao
Summary: In this study, a simple method for the synthesis of 2-azidoimines through azidoamination reactions was reported. The synthetic potential of the method was further demonstrated through sequential condensation/amination reactions and chemoselective, orthogonal transformations, leading to the access of biologically active unsymmetrical diamines.
Article
Chemistry, Organic
Cheng Wang, Biao Liu, Zeyu Shao, Junqi Zhou, Andong Shao, Liang-Hua Zou, Jian Wen
Summary: A procedure for the mild synthesis of 1,2-diamines without the need for a catalyst and oxidizing reagent has been developed. This method demonstrated practicality through one-pot synthesis, scale-up reaction, and transformation of products. Mechanistic studies revealed the crucial role of aziridine formation in this diamination process.
Article
Chemistry, Multidisciplinary
Yu Zheng, Zhu-Jun Wang, Zhi-Peng Ye, Kai Tang, Zhen-Zhen Xie, Jun-An Xiao, Hao-Yue Xiang, Kai Chen, Xiao-Qing Chen, Hua Yang
Summary: A metal-free photosensitized protocol for regioselective diamination of alkene feedstocks was developed. The reaction proceeds in a single step and yields differentially protected 1,2-diamines in moderate to high yields. Mechanistic studies reveal that the excellent regioselectivity is due to the large reactivity difference between two different N-centered radical species.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Nutrition & Dietetics
Maria Bikaki, Nikolai Kuhnert
Summary: This study investigates the thermal degradation of dietary-relevant pentapeptides and proposes a degradation mechanism similar to lipid peroxidation, forming novel degradation products with potential toxicological relevance. A radical-based reaction mechanism is proposed, leading to distinct reaction products with specific functionalities.
FRONTIERS IN NUTRITION
(2021)
Article
Chemistry, Organic
Yali Liu, Yu Wei, Zhen Yang, Yang Li, Yan Liu, Ping Liu
Summary: In this study, a successful C3-H direct iodination reaction was reported for the synthesis of novel 3-iodopyrrolo[1,2-a]quinoxaline derivatives, with significant promotion of selectivity and conversion by a catalytic amount of p-toluenesulfonic acid. The reaction can be scaled up to gram level, and the iodinated products can be further transformed into biologically active compounds through palladium-catalyzed coupling reactions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Lei Zhang, Chengyu Liu, Maolin Sun, Chaoming Liang, Liming Cao, Xiantong Yao, Yueyue Ma, Ruihua Cheng, Jinxing Ye
Summary: An iridium catalytic system using a ferrocene-based phosphine ligand with a modular and tunable unsymmetrical vicinal diamine scaffold was developed for the asymmetric hydrogenation of aryl ketones. This method provided a powerful tool for the enantioselective synthesis of diverse chiral alcohols, exhibiting excellent reactivity and enantioselectivity (yield up to 99%, ee up to 99%, and turnover number up to 50,000). The substituents and chirality of unsymmetrical diamines in the ligands played a crucial role in achieving satisfactory results.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Dou-Dou Chen, Song-Lin Zhang
Summary: This study reports the geminal amino- and oxy-trifluoromethylation of ortho-ethynyl anilines/ phenols using phenCu(III)(CF3)(3), which provides a concise and controllable synthesis of valuable trifluoromethylated N and O-heterocyclic compounds. The method circumvents the regioselectivity issue often encountered in C H trifluoromethylation of arenes/heteroarenes and suppresses the competing vicinal fluoro-trifluoromethylation of terminal alkynes. The synthetic value of Cu(III) CF3 compounds in medicinal chemistry is highlighted.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Medicinal
Cindy Patinote, Carine Deleuze-Masquefa, Kamel Hadj Kaddour, Laure-Anais Vincent, Romain Larive, Zahraa Zghaib, Jean-Francois Guichou, Mona Diab Assaf, Pierre Cuq, Pierre-Antoine Bonnet
Summary: Melanoma, the most aggressive skin cancer, causes several thousand deaths each year, posing a significant public health concern. New compounds based on specific structures show potential therapeutic effects for melanoma, demonstrating interesting cytotoxic activity in vitro.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Ramachandra Reddy Putta, Simin Chun, Seok Beom Lee, Junhwa Hong, Dong-Chan Oh, Suckchang Hong
Summary: In this study, an iron-catalyzed one-pot synthesis of quinoxalines was reported using 2-nitroanilines and vicinal diols via transfer hydrogenative condensation. The method has the advantages of no need for additional reagents and generating water as the sole byproduct.
