Article
Chemistry, Multidisciplinary
Liyan Fu, Jingwen You, Yasushi Nishihara
Summary: This method utilizes a palladium catalyst to synthesize unsymmetrical biaryls by cross-coupling acyl chlorides with potassium perfluorobenzoates under redox-neutral conditions. Compared to traditional methods, this synthetic strategy allows for the easy preparation of reactants from inexpensive aromatic carboxylic acids.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Lucie Finck, Sarah Dabrowski, Martin Oestreich
Summary: A denitrogenative palladium-catalyzed C(sp(2))-C(sp(2)) cross coupling reaction of aryl-substituted diazenes capped with a trimethylsilyl group and functionalized aryl bromides is described. The use of a PEPPSITM catalyst in the presence of NaOt-Bu enables the activation of the N-aryl-N'-silyldiazene pronucleophile, leading to the loss of dinitrogen and subsequent coupling with the in-situ-formed aryl nucleophile. This methodology provides access to biaryl compounds with various substituents.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Inorganic & Nuclear
Francois Mazars, Guillermo Zaragoza, Lionel Delaude
Summary: The alkylation of caffeine with methyl iodide led to the synthesis of a new compound. Three complexes were obtained through multiple steps and were found to be highly active catalysts for the Suzuki-Miyaura cross-coupling reaction. The reaction showed high yields and could be carried out in a green solvent with low catalyst loading and in the presence of air.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2022)
Review
Biochemistry & Molecular Biology
Rida Noor, Ameer Fawad Zahoor, Muhammad Irfan, Syed Makhdoom Hussain, Sajjad Ahmad, Ali Irfan, Katarzyna Kotwica-Mojzych, Mariusz Mojzych
Summary: Hiyama cross-coupling is a versatile reaction that enables the construction of carbon-carbon bonds in synthetic organic chemistry. By coupling organosilicons with organic halides using transition metal catalysts, good yields and high enantioselectivities can be achieved. In recent years, researchers have made significant progress in using the Hiyama coupling reaction for the synthesis of diversified natural products and pharmaceutical drugs.
Article
Chemistry, Organic
Xiao-lin Cui, Hao-yu Tian, Shuo-jin Wang, Xun Chen, Du-lin Kong
Summary: A regioselective metal-free sulfenylation of imidazoheterocycles with heterocyclic thiols or thiones has been achieved using a cross-dehydrogenative coupling method in water. The procedure offers advantages such as green solvents, absence of foul-smelling sulfur sources, and mild conditions, making it highly applicable in the pharmaceutical industry.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Kiyoshi Tanemura
Summary: The addition of small amounts of dioxane and water was beneficial in solvent-free Suzuki-Miyaura cross-coupling reactions. Various solid and liquid aryl bromides and chlorides reacted with boronic acids in the presence of 1 mol% of Pd(OAc)2 and 2 mol% of RuPhos at 25°C to yield the corresponding biaryls with good to excellent yields. The reactions of aryl chlorides were faster than those of aryl bromides. 0.2 mol% of Pd(OAc)2 was sufficient for the reactions of some aryl chlorides. This procedure is particularly useful for the reactions of aryl chlorides.
Article
Chemistry, Organic
Alejandro Cervantes-Reyes, Aaron C. Smith, Gary M. Chinigo, David C. Blakemore, Michal Szostak
Summary: This study reports a method for the direct synthesis of nitrogen-containing heteroaromatic biaryls by decarbonylative Pd-catalyzed Suzuki cross-coupling. The practical and modular nature of this method enables the synthesis of diverse heterobiaryl products in excellent yields.
Article
Chemistry, Multidisciplinary
Guipeng Feng, Jie Meng, Shaohong Xu, Yao Gao, Yingying Zhu, Ziyu Huang
Summary: A novel Cu-catalyzed radical-radical cross coupling reaction of 3-aminoindazoles with sulfonyl hydrazides has been developed, providing a convenient and efficient synthesis of diverse 1,3-substituted aminoindazoles. This methodology offers readily available starting materials, wide substrate scope, and operational simplicity. Notably, gram-scale reactions have been successfully demonstrated.
Article
Chemistry, Physical
Guang-Yan Xing, Ya-Cheng Zhu, Deng-Yuan Li, Pei-Nian Liu
Summary: On-surface synthesis, a powerful tool for atomically precise fabrication of low-dimensional carbon nanomaterials, has greatly enriched fundamental science and technology. Achieving high selectivity of covalent coupling reactions remains challenging due to the complicated reactivity of organic groups and irreversibility of covalent bonds. Only a few on-surface covalent coupling reactions are frequently used, and this Perspective focuses on the development and synthetic applications of on-surface cross-coupling reactions.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Inorganic & Nuclear
Xuelei Guo, Hester Dang, Steven R. Wisniewski, Eric M. Simmons
Summary: This study reports the development of a Ni-catalyzed Suzuki-Miyaura cross-coupling reaction using an aqueous amine base as a catalyst. The reaction exhibits high catalytic activity and low metal loadings, while tolerating various functional groups. Additionally, the method is applicable to complex pharmaceutical substrates.
Article
Chemistry, Multidisciplinary
Sumanth Hegde, Aatika Nizam, Ajesh Vijayan, Ramesh B. Dateer, Suresh Babu Naidu Krishna
Summary: We have developed a magnetically recyclable palladium nanocatalyst capable of efficiently catalyzing the Suzuki-Miyaura cross-coupling reaction in an ethanol/water solution under ultrasonic conditions. The catalyst is compatible with various aryl halides and aryl boronic acids and exhibits excellent stability, low leaching, and heterogeneous nature.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Liangzhi Pang, Qilin Sun, Zhan Huang, Gen Li, Jiaojiao Liu, Jiaxu Guo, Chuanzhi Yao, Jie Yu, Qiankun Li
Summary: A palladium-catalyzed stereoselective cleavage of the C-P bond has been developed for the synthesis of atropisomers with a P-stereogenic center. The method offers high yields and high stereoselectivity, and the resulting product shows potential as a chiral catalyst in phosphine-catalyzed cycloaddition reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Xinlan A. F. Cook, Loic R. E. Pantaine, David C. Blakemore, Ian B. Moses, Neal W. Sach, Andre Shavnya, Michael C. Willis
Summary: Heteroaromatic sulfinates are effective nucleophilic reagents in Pd-0-catalyzed cross-coupling reactions with aryl halides. Base-activated, latent sulfinate reagents, such as beta-nitrile and beta-ester sulfones, have been introduced to address challenges in purifying and solubilizing metal sulfinate salts, as well as their tolerance to multi-step transformations. These latent sulfinate reagents have proven to be stable through multi-step substrate elaboration and amenable to scale-up processes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Jaime Ponce-de-Leon, Pablo Espinet
Summary: Highly selective cross-coupling reactions to polyfluorinated assymmetric biaryls, including the symmetric biaryl C6F5-C6F5, were achieved at relatively low temperature (80 degrees C) and in short times using [MCl2(PhPEWO-F)] catalysts (M = Ni, Pd), with (ArI)-I-F and Zn(C6F5)(2) as examples of highly fluorinated nucleophiles.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Jun Chen, Yu-Jie Liang, Peng-Zi Wang, Guo-Qing Li, Bin Zhang, Hao Qian, Xiao-Die Huan, Wei Guan, Wen-Jing Xiao, Jia-Rong Chen
Summary: This study presents a photoinduced copper-catalyzed cross-coupling reaction for the generation of allylic esters. The reaction proceeds at room temperature with high regio- and enantioselectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
