Article
Chemistry, Multidisciplinary
Remi Lavernhe, Ruben O. Torres-Ochoa, Qian Wang, Jieping Zhu
Summary: A versatile copper-catalyzed synthesis of ynimines from readily available O-acetyl ketoximes and terminal alkynes has been developed, leading to the synthesis of medicinally important heterocycles.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Xin-Shen Liang, Rui-Dong Li, Wei Sun, Zhong Liu, Xiao-Chen Wang
Summary: Borane-mediated hydride abstraction has been shown to be a powerful tool for the C(sp(3))-H functionalization of amines, but its activity with ethers is still unknown. In this study, we discovered this activity in 2H-chromenes and established a catalytic C(sp(3))-H functionalization reaction using silyl ketene acetals as nucleophiles.
Article
Chemistry, Applied
Fernando Martinez-Lara, Anisley Suarez, Noelia Velasco, Samuel Suarez-Pantiga, Roberto Sanz
Summary: The gold-catalyzed transformation of propargylic glycols with thiols results in the formation of alpha-indol-3-yl alpha-((Z)-2-thioalkenyl) ketones through a complex but selective reaction mechanism. This sequence involves regioselective thiolation of indolyl diols followed by the attack of sulfur on the activated alkyne, rather than the indole. The final compounds are obtained in high yields from simple starting materials such as indolyl acyloins, ethynyl magnesium bromide, and thiols.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Miguel A. Munoz-Torres, Fernando Martinez-Lara, Marta Solas, Samuel Suarez-Pantiga, Roberto Sanz
Summary: The combination of organolithium chemistry with gold catalysis offers a new synthetic strategy for accessing polysubstituted indoles and carbazoles. This method utilizes ketopyrroles as starting materials and involves a series of reactions to selectively synthesize the desired products.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Cristian Cavedon, Sebastian Gisbertz, Susanne Reischauer, Sarah Vogl, Eric Sperlich, John H. Burke, Rachel F. Wallick, Stefanie Schrottke, Wei-Hsin Hsu, Lucia Anghileri, Yannik Pfeifer, Noah Richter, Christian Teutloff, Henrike Mueller-Werkmeister, Dario Cambie, Peter H. Seeberger, Josh Vura-Weis, Renske M. van der Veen, Arne Thomas, Bartholomaus Pieber
Summary: We demonstrate visible-light-mediated carbon-heteroatom cross-coupling reactions using a photoactive Ni(II) precatalyst. The activation of this precatalyst involves an initial intraligand charge transfer event triggered by visible light irradiation. Additionally, a porous, recyclable organic polymer for heterogeneous nickel catalysis of cross-coupling reactions is obtained through ligand polymerization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Dominik Birnthaler, Rok Narobe, Eliseo Lopez-Berguno, Christoph Haag, Burkhard Koenig
Summary: Ligand-to-metal charge transfer (LMCT) photo-catalysis enables the activation and utilization of halides and other heteroatoms in metal complexes. The application of bismuth LMCT in organic radical coupling reactions has been expanded, generating chlorine and carboxyl radicals in net-oxidative and redox-neutral photochemical reactions. The study reveals BiCl4- and BiCl52- as the catalytically active bismuth species under 385 nm irradiation, providing insight into the reactivity of the highly reactive bismuth(II) catalyst fragment through cyclic voltammetry and UV-vis studies.
Review
Chemistry, Applied
Seoung-Mi Choi, Ju Hyun Kim
Summary: This review summarizes the progress made in the synthesis of 2H-pyrroles since 2000, including methods such as dearomatization of 1H-pyrrole, oxidation of pyrrolines or pyrrolidines, ring construction via catalytic cycloaddition, and rearrangement of 3H-pyrroles.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Chengqiang Cao, Yi Yang, Xin Li, Yunxia Liu, Hui Liu, Zengdian Zhao, Lei Chen
Summary: The reaction, catalyzed by palladium, efficiently constructs two new bonds with high yields, while the alkene group is easily functionalized, leading to the formation of products with a unique structure that is difficult to synthesize.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Jialu Chen, Ruiqin Zhang
Summary: This study investigates the influence of phosphine ligands on cross-coupling reactions and proposes a descriptor %V-bur (min) - 3 center dot HOMO-LUMO gap (eV) to reveal the ligands' effects. The yields of the reactions are plotted against the descriptor on volcano plots to optimize the reaction yields.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2022)
Article
Biochemistry & Molecular Biology
Christian Frabitore, Jerome Lepeule, Tom Livinghouse
Summary: Nitrogen-containing heterocycles are the main components of most FDA-approved small-molecule pharmaceuticals. This article describes a synthetic method to produce saturated N-heterocyclic drug scaffolds with an internal alkyne. By treating compounds and conducting reactions, products such as piperidines and pyrrolidines can be obtained.
Article
Chemistry, Physical
Rajender Nallagonda, Djamaladdin G. Musaev, Rashad R. Karimov
Summary: Partially saturated nitrogen heterocycles are versatile building blocks that can be used to synthesize other nitrogen heterocycles. Coupling reactions between aryl iodides and pyridinium or other heteroarenium salts can produce a wide range of nitrogen heterocycle scaffolds. This method has high operability and good tolerance towards functional groups.
Article
Biochemistry & Molecular Biology
Sofia Siciliano, Elena Cini, Maurizio Taddei, Giorgia Vinciarelli
Summary: The synthesis of 2-substituted indoles from unprotected 2-alkynylanilines using Pd(OAc)(2) catalyst in 3% TPGS-750-M water was found to be sensitive to the heating mode and the MW delivery mode, with convectional heating often proving more effective than microwave dielectric heating. Additionally, a tandem Sonogashira-cyclisation reaction was successfully achieved in the nanomicellar water environment with Pd(OAc)(2)/Xphos.
Article
Chemistry, Multidisciplinary
Feixiang Sun, Jiamin Huang, Zhihong Wei, Conghui Tang, Weiping Liu
Summary: A homogeneous manganese-catalyzed cross-coupling reaction of secondary alcohols was developed for the synthesis of gamma-disubstituted alcohols and beta-disubstituted ketones. The protocol, using Mn-MACHO(Ph) as the catalyst, exhibited a wide substrate scope and good functional group tolerance, resulting in diverse valuable disubstituted alcohols and ketones in moderate to good yields. The selective formation of alcohol products was found to be influenced by reaction temperature, with alcohols favored over ketones at lower temperatures.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Bijan Mirabi, Austin D. Marchese, Mark Lautens
Summary: In this study, a nickel-catalyzed cross-electrophile coupling reaction of aryl chlorides and heteroaryl chlorides was reported, enabled by a synergistic combination of halide effects and the addition of a magnesium salt. Electronic-deficient aryl chlorides were found to perform the best in the reaction, and preliminary mechanistic evidence showed that MgCl2 is crucial for accelerating the reduction of Ni(II) while small quantities of iodide lead to improved yields.
Review
Chemistry, Organic
C. M. A. Afsina, Thaipparambil Aneeja, Mohan Neetha, Gopinathan Anilkumar
Summary: Copper-catalyzed organic reactions have attracted widespread attention due to the abundance and affordability of copper, as well as its low toxicity, eco-friendliness, sustainable nature, and versatility as a catalyst. These reactions are primarily used for the synthesis of biologically important nitrogen heterocycles, amines, amides, imines, and alkynes.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
