The cobalt-catalyzed chelation-assisted iodination of aromatic amides using molecular I as an iodinating reagent is reported. 8-Amino-5-chloroquinoline functions as an efficient directing group. This mild and air stable catalytic system shows a wide functional group tolerance and improved synthetic accessibility.
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http://dx.doi.org/10.1039/c7cc08457a | DOI Listing |
Water Res
January 2025
Shanghai Key Lab for Urban Ecological Processes and Eco-Restoration, School of Ecological and Environmental Sciences, East China Normal University, Shanghai 200241, China; Technology Innovation Center for Land Spatial Eco-restoration in Metropolitan Area, Ministry of Natural Resources, 3663N. Zhongshan Road, Shanghai 200062, China; Shanghai Engineering Research Center of Biotransformation of Organic Solid Waste, Shanghai 200241, China; State Key Laboratory of Estuarine and Coastal Research, Shanghai 200241, China. Electronic address:
Chemistry
January 2025
Ruprecht Karls Universitat Heidelberg, Organisch-Chemisches Institut, Im Neuenheimer Feld 270, 69120, Heidelberg, GERMANY.
Here we present a simple gold-catalyzed one-pot reaction of easily available diarylbutadiynes, with trimethoxybenzene as solvent and reactant to synthesize 4,6,8-trimethoxyazulenes. The methoxy substituents, which render the azulene very electron-rich, enable a change of azulenes typical regioselectivity for electrophilic substitutions, which enables facile electrophilic 2-substitution with iodine, bromine, chlorine, selenium or sulfur. Especially the 2-haloazulenes which can usually only be obtained through lengthy multistep syntheses are valuable building blocks for the synthesis of 2-substituted azulene derivatives.
View Article and Find Full Text PDFChem Commun (Camb)
January 2025
College of Pharmaceutical Sciences, Ritsumeikan University, Kusatsu 525-8577, Shiga, Japan.
We have developed transition-metal-free synthetic methodologies for dibenzoxazepinones utilizing salicylamides as starting materials and employing two distinct types of successive hypervalent iodine-mediated arylocyclizations. This synthetic protocol encompasses selective phenol -arylation of salicylamides with diaryliodonium salts, followed by electrophilic aromatic amination utilizing chemically or electronically generated hypervalent iodine reagents in the second stage of the process.
View Article and Find Full Text PDFEnviron Sci Technol
January 2025
State Key Laboratory of Pollution Control and Resources Reuse, College of Environmental Science and Engineering, Tongji University, Shanghai 200092, China.
Iodinated DBPs (I-DBPs), many more toxic than regulated chlorinated and/or brominated DBPs, are a major challenge in the supply of safe drinking water. While over 800 DBPs have been identified, the occurrence and precursors of toxic I-DBPs remain poorly understood. Herein, natural organic matter from two raw drinking waters was fractionated using ultrafiltration membranes into different groups based on molecular weight (MW).
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306, United States.
We present a six-step cascade that converts 1,3-distyrylbenzenes (-stilbenes) into nonsymmetric pyrenes in 40-60% yields. This sequence merges photochemical steps, ,-alkene isomerization, a 6π photochemical electrocyclization (Mallory photocyclization); the new bay region cyclization, with two radical iodine-mediated aromatization steps; and an optional aryl migration. This work illustrates how the inherent challenges of engineering excited state reactivity can be addressed by logical design.
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