In this study, we developed a metal-free and highly chemoselective method for the reduction of aromatic nitro compounds. This reduction was performed using tetrahydroxydiboron [B(OH)] as the reductant and 4,4'-bipyridine as the organocatalyst and could be completed within 5 min at room temperature. Under optimal conditions, nitroarenes with sensitive functional groups, such as vinyl, ethynyl, carbonyl, and halogen, were converted into the corresponding anilines with excellent selectivity while avoiding the undesirable reduction of the sensitive functional groups.
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http://dx.doi.org/10.1021/acs.joc.1c01431 | DOI Listing |
Org Lett
January 2025
College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi'an 710021, China.
Capturing CO is highly valued in the field of organic synthesis, especially underdeveloped dual-CO conversion. In this study, we detail a novel reductive cyclization of 2-indolylanilines with dual CO as a difunctional reagent in the presence of PMHS [poly(methylhydrosiloxane)], delivering methyl-substituted quinoxalines. Furthermore, another chemoselective cyclization with 2-pyrrolylanilines is also realized by converting mono-CO.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology (ECUST), Shanghai 200237, China.
A highly efficient base-controlled synthesis of -β-trifluoromethyl-substituted 2-benzo[]imidazole-2-thiones and 2-fluoro-4-benzo[4,5]imidazo[2,1-][1,3]thiazines hydroamination or defluorinative cyclizations of α-(trifluoromethyl)styrenes with 2-mercaptobenzimidazole was developed.
View Article and Find Full Text PDFJ Org Chem
January 2025
Key Laboratory of Novel Targets and Drug Study for Neural Repair of Zhejiang Province, School of Medicine, Hangzhou City University, Hangzhou, Zhejiang 310015, China.
Reported herein is a concise synthesis of sulfoximidoyl amidines enabled by a Pd-catalyzed cascade aza-Claisen rearrangement and nucleophilic reaction at room temperature. Free -sulfoximines and -allylynamides were employed as the modular building blocks to produce the expected sulfoximine amidine derivatives in highly chemoselective models and in 100% atom efficiency. A broad range of functional groups were well tolerated under these gentle reaction conditions to give the desired products in generally good to excellent yields.
View Article and Find Full Text PDFMolecules
December 2024
Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, China.
In this study, an iridium-catalyzed selective 1,4-reduction of α,β-unsaturated carbonyl compounds is realized, with water as a solvent and formic acid as a hydride donor. The new efficient iridium catalyst features a 2-(4,5-dihydroimidazol-2-yl)quinoline ligand. The chemoselectivity and catalyst efficiency are highly dependent on the electronic and steric properties of the substrates.
View Article and Find Full Text PDFMolecules
December 2024
State Key Laboratory Incubation Base for Green Processing of Chemical Engineering, School of Chemistry and Chemical Engneering, Shihezi University, Shihezi 832003, China.
In the category of drugs approved by the U.S. FDA, pyrrolidine is the most frequently used core of five-membered nonaromatic heterocycles containing nitrogen.
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