Article
Chemistry, Organic
Zeng-Hui Lin, Yu-Fei Yao, Cheng-Pan Zhang
Summary: Deuteration of arylthianthren-S-ium triflates with CD3OD or CD3OD/CD3COCD3 in the presence of Cs2CO3 by palladium catalysis or photoirradiation allows for the convenient synthesis of deuterated arenes in good yields. The Pd-catalyzed reaction generally gives better yields than the photoinduced deuteration, but exceptions exist. These reactions highlight eco-friendly conditions, simplicity, inexpensive deuterium sources, good functional group tolerance, and a range of substrates. This protocol provides a high selectively formal aromatic C-H deuteration for efficient deuterium labeling of multifunctionalized arenes and drug molecules.
Article
Chemistry, Organic
Na-Na Ma, Jing-Ao Ren, Xiang Liu, Xue-Qiang Chu, Weidong Rao, Zhi-Liang Shen
Summary: The direct cross-couplings of aryl sulfonium salts with aryl halides using nickel as a reaction catalyst were successfully achieved. The reactions proceeded efficiently via C-S bond activation at ambient temperature, providing moderate to good yields, potentially serving as an attractive alternative to conventional cross-coupling reactions.
Article
Chemistry, Multidisciplinary
Tongchang Fang, Liwei Wang, Miaomiao Wu, Xiaotian Qi, Chao Liu
Summary: The synthesis of diborodichloromethane (DBDCM) is crucial for the construction of diverse gem-diborylalkanes, and consecutive tetra-functionalizations of DBDCM allow for the construction of diverse carbon-containing molecules. Isotopically enriched C-13-DBDCM and B-10-DBDCM reagents are beneficial for the synthesis of carbon-13 and boron-10 molecules.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Shi-Zhong Tang, Kai Xiang, Rui Ye, Meng-En Chen, Jian-Chang Yu, Zhi-Juan He, Fu-Min Zhang
Summary: A novel thio-Ritter reaction has been discovered, providing a straightforward approach for the synthesis of important thioamides. This reaction exhibits a broad substrate scope, operational simplicity, utilization of available feedstock chemicals, and the ability for late-stage functionalization of bioactive molecules. The reaction mechanism has also been proposed.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Qiyue Wang, Xinyu Hao, Kun Jin, Rong Zhang, Chunying Duan, Yaming Li
Summary: A novel photo-induced C-H arylation of (hetero)arenes using aryl selenonium salts as an aryl source has been developed. The method involves C-Se bond activation under blue LED irradiation, enabling the arylation of aromatic (hetero)cyclic compounds. The method utilizes safe and clean energy and yields site-selective biphenyl or bi-heterocyclic products in medium to good yields. In addition, the borylation and Sonogashira coupling of aryl selenonium salts also proceed in good yields. Results demonstrate that selenonium salts are more reactive than sulfonium salts.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Janos T. Csenki, Balazs L. Toth, Ferenc Beke, Balint Varga, Peter P. Feher, Andras Stirling, Zsuzsanna Czegeny, Attila Benyei, Zoltan Novak
Summary: This study reports a novel dyotropic rearrangement process involving the migration of iodine atoms in alkyl fragments, demonstrated through experimental and DFT studies. A new fluoroalkyl iodonium reagent was designed and synthesized using the dyotropic rearrangement, showing excellent fluoroalkylation activity towards various amines and nitrogen heterocycles.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Carlos Corral Suarez, Ignacio Colomer
Summary: This study presents a method for trifluoromethylarylation of alkenes using anilines, without the need for additives, transition metals, photocatalysts, or excess reagents. The key role of hexafluoroisopropanol (HFIP) as a unique solvent, which establishes a hydrogen bonding network with aniline and trifluoromethyl reagent, is revealed through a detailed mechanistic study. This work unlocks the use of anilines in the selective trifluoromethylarylation of olefins via a mild protocol that avoids transition metals, expensive photocatalysts, and additives.
Article
Chemistry, Organic
Hikaru Nakahara, Junichiro Yamaguchi
Summary: This study reports a 1,2-migration (aryl dance reaction) of the aryl group on heteroles. It was found that AlCl3 can efficiently convert C3-arylheteroles to C2-arylheteroles, and depending on the electron density of the substrate, catalytic Zn(OTf)2 can also facilitate the conversion from C2 to C3-arylheteroles. Additionally, a one-pot aryl dance/acylation or bromination and arylation/aryl dance cascade was demonstrated.
Article
Chemistry, Organic
Petra Kralova, Katerina Zakova, Lenka Pospisilova, Miroslav Soural
Summary: 2,3-Disubstituted quinoline-4-carbonitriles were synthesized through a series of reactions using various starting materials, and some of the prepared compounds showed moderate activity against E. coli.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Wen Liu, Yan Zhang, Shuya Xing, Huilin Lan, Xinrui Chen, Ying Bai, Xinxin Shao
Summary: beta-Trifluorosulfinylesters were developed as novel reagents for direct trifluoromethylthiolation and trifluoromethylsulfinylation reactions. These reagents could be easily prepared in three steps without column purification, using inexpensive commercially available starting materials. The switchable reactivity of the reagents was controlled by different activators, with the formation of fluorinated sulfenate anions under basic conditions and fluorinated sulfonium salts under the presence of Tf2O. The fluorinated sulfonium salts served as electrophilic synthons for transition-metal-free C-H trifluoromethylthiolation of electron-rich arenes and alkenes.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Grant N. Shivers, F. Christopher Pigge
Summary: This experiment presents a straightforward method for the preparation of N-alkenyl-2-pyridones in one pot, utilizing easily available reagents. The reaction displays high diastereoselectivity and tolerance towards a variety of aldehyde reaction partners. Furthermore, the resulting pyridone products are versatile and can be further manipulated to form N-alkyl pyridones and polycyclic ring systems.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jiwen Jiao, Xiaoming Wang
Summary: A new method has been disclosed, which combines electron-transfer-induced activation with 1,2-metalate rearrangement to efficiently convert aromatic amides into biologically relevant diarylmethylamines. This reaction, with its simplicity and versatility, shows great promise for the synthesis of amines, potentially opening up new avenues in retrosynthetic planning and finding widespread use in academia and industry.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Thomas Sephton, Anastasios Charitou, Cristina Trujillo, Jonathan M. Large, Sam Butterworth, Michael F. Greaney
Summary: This study found that benzyne can be used to activate anilines and set up aryl transfer reactions in a single step, establishing a metal-free route to valuable biaryl products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Lei Zhang, Wangzhen Bao, Yuchen Liang, Wenjing Pan, Dongyang Li, Lichun Kong, Zhi-Xiang Wang, Bo Peng
Summary: This study demonstrates the reversal of stereoselectivity in MBH-type [3,3]-rearrangement by using a new pair of rearrangement partners, leading to the synthesis of different types of alpha-aryl alpha,beta-unsaturated carbonyl derivatives. Mechanistic studies provide insights into the reaction pathway and the opposite stereoselectivities observed.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Biochemistry & Molecular Biology
Ji-Wei Zhang, Shao-Hua Xiang, Shaoyu Li, Bin Tan
Summary: The article presents an efficient synthetic route to access important atropisomers with biaryl frameworks through copper-catalyzed reactions, featuring mild conditions, good substrate compatibility, and excellent efficiency. The practicality of this protocol was further extended by the synthesis of biaryl amino alcohols.
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)
