Article
Chemistry, Multidisciplinary
Zhuang Wang, Kaikai Niu, Yuxiu Liu, Hongjian Song, Qingmin Wang
Summary: A mild and convenient protocol for the synthesis of alpha-alkoxy isochroman derivatives has been reported in this study. The electrochemical alpha-C(sp(3))-H/O-H cross-coupling reactions of isochromans and alcohols in the presence of benzoic acid were used, which facilitated the electro-oxidation process and increased the product yield. The desired coupling products were obtained in moderate to high yields.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Chao Li, Ran Ding, Heng-Yi Guo, Shuang Xia, Lei Shu, Pei-Long Wang, Hongji Li
Summary: In this study, we report a rare catalyst-free electrochemical cross-coupling reaction that can forge various types of chemical bonds at room temperature. The study also reveals the dual role of organotrifluoroborates as both coupling partner and electrolyte in the C-H functionalization reaction.
Article
Chemistry, Organic
Edwin Alfonzo, Sudhir M. Hande
Summary: The study reports the C-H activation of thioethers and their addition to N-methoxyheteroarenium salts to synthesize alpha-heteroaromatic thioethers. It reveals a two-step activation mechanism, with N-methoxyheteroarenium salts playing multiple roles in the reaction process.
Article
Chemistry, Inorganic & Nuclear
Ishfaq Ibni Hashim, Thomas Scattolin, Nikolaos V. Tzouras, Laurens Bourda, Kristof Van Hecke, Ida Ritacco, Lucia Caporaso, Luigi Cavallo, Steven P. Nolan, Catherine S. J. Cazin
Summary: This study reports a synthetic approach to monomeric copper-alkynyl and copper-thiolato complexes of the type [(NHC)Cu(R)] (R = alkynyl or thiolato) using a weak base method. The reactions proceed under mild conditions in air and environmentally acceptable solvents. The importance of the steric properties of the supporting NHC ligand in stabilizing mononuclear complexes is discussed.
DALTON TRANSACTIONS
(2021)
Article
Chemistry, Organic
Yang Song, Hao Zhang, Jiabao Guo, Yifei Shao, Yuzhou Ding, Li Zhu, Xiaoquan Yao
Summary: This work presents a visible-light-induced oxidative alpha-alkylation of glycine derivatives with ethers using Eosin Y as a catalyst. The reaction, conducted under blue light from a 3 W LED, produces a range of alpha-etherized glycine derivatives with good to excellent yields and functional group tolerance when tert-butyl hydroperoxide is used as the oxidant at ambient temperature. This operationally easy procedure offers an economical, metal-free, and mild approach for synthesizing alpha-etherized glycine derivatives.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Akanksha Singh Baghel, Amit Kumar
Summary: In this study, we developed a ruthenium(ii)-catalyzed weakly coordinating primary amide-assisted ortho-di-alkynylation of (hetero)arylamides via double C-H bond activation using bromo-alkynes as coupling partners. The strategy demonstrated attractive features including the use of inexpensive ruthenium(ii)-salt, external auxiliary-free directing group, simple reaction conditions, broad substrate scope, high reaction yields, and scalability of the synthesis.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Liang Hu, Guangrong Meng, Jin-Quan Yu
Summary: This study reports the first Pd(II)-catalyzed intermolecular fi-methylene C(sp3)-H arylation of free aliphatic acids using bidentate pyridine-pyridone ligands. The bite angle of the ligand plays a key role in promoting fi-methylene C-H activation of free carboxylic acid. This transformation provides a disconnection for alkylation of arenes with simple aliphatic acids.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Review
Chemistry, Multidisciplinary
Erika L. Lucas, Nelson Y. S. Lam, Zhe Zhuang, Hau Sun Sam Chan, Daniel A. Strassfeld, Jin-Quan Yu
Summary: CONSPECTUS: The development of asymmetric beta-C-H activation reactions for organic synthesis has been described in this Account. By studying reaction mechanisms and stereochemical properties, both strongly coordinating and weakly coordinating directing groups were designed to achieve beta-C-H activation of aliphatic acids and carboxylic acids, respectively. The development of five classes of chiral ligands enabled enantioselective beta-C-H activation reactions of readily available substrates.
ACCOUNTS OF CHEMICAL RESEARCH
(2022)
Article
Chemistry, Organic
Lei Liang, Ge Guo, Chen Li, Song-Lin Wang, Yue-Hui Wang, Hai-Ming Guo, Hong-Ying Niu
Summary: The study demonstrates Cu-catalyzed intermolecular alkynylation and allylation of unactivated C(sp(3))-H bonds with SOMO-philes via HAT, using N-fluoro-sulfonamide as a reagent, resulting in high yields, good regioselectivity, and functional-group compatibility. Late-stage functionalization of natural products and drug molecules is also shown in the research.
Article
Chemistry, Organic
Lin Ma, Xiaohui Zhang, Yanyan Tuo, Qing-Zhong Zheng
Summary: An efficient Cp*Rh(III)-catalyzed regioselective C(sp(2))-H mono- and dialkynylation of thioamides was described. This reaction was performed under mild conditions with high yields, demonstrating versatility by controlled mono- and dialkynylation. The application of this approach in late-stage functionalization of two drug molecules (Adapalene and Amoxapine) was also demonstrated.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Rui-Qi Wang, Qing-Hui Jiang, Hui-Xiang Wang, Xiao-Wei Zhang, Nan Yan
Summary: An efficient electrochemical dehydrogenative cross-coupling of benzylic C-H bonds with 1-thiosugars at room temperature is reported, providing facile access to various glycosylated xanthene derivatives with high yields. This reaction exhibits high atom economy, efficiency, mild reaction conditions, environmental friendliness, and excellent functional group tolerance. Preliminary mechanistic investigations suggest that the reaction proceeds through a free radical process.
Article
Chemistry, Organic
Xinjie Li, Peng Qi, Hongguang Du
Summary: A metal-free cross-dehydrogenation coupling method was developed for the synthesis of N-9 alkylated purine derivatives. Thioethers were used as versatile alkylation reagents with PhI(OAc)2 as the oxidant, resulting in moderate to good yields. The regioselectivity of this method involving unsymmetrical thioethers and purine derivatives was also investigated.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Man Wang, Ming Li, Long Zhang, Ran Song, Daoshan Yang, Jian Lv
Summary: Photoredox catalysis involving Ir-III in combination with DABCO as a dual hydrogen-bonding donor and organic base can enable the direct gamma-C(sp(3))-H activation of saturated alpha-keto esters, leading to the synthesis of various 4-indolyl substituted 2-hydroxy-3-enoic acid esters. This method offers high yields and high enantioselectivity.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Zhuang Wang, Yuxiu Liu, Hongjian Song, Qingmin Wang
Summary: In this study, we developed an electrochemical protocol for the synthesis of hemiaminal ethers containing tetrahydrofuran rings. The protocol involves alpha-C(sp(3))-H/N-H cross-coupling reactions between tetrahydrofuran and sulfonamides or amides, and does not require a chemical oxidant. The reaction can be conducted at room temperature, and provides moderate to high yields of the desired products.
Article
Multidisciplinary Sciences
Takafumi Yatabe, Kazuya Yamaguchi
Summary: This article reports a gold nanoparticles-catalyzed alpha-methylene alkynylation of tertiary amines, which exhibits regioselectivity and selectivity. This method provides an important approach for the development of novel medicines.
NATURE COMMUNICATIONS
(2022)
