A one-pot preparation of the 2,2'-dibromo-1,1'-bisheteroarenes 3a-d from bromo-heteroarenes utilizing the sequence of the base-catalyzed halogen dance (BCHD) reaction and CuCl(2)-promoted oxidative coupling of the in situ formed alpha-lithio-beta-halo-heteroarenes 2a-d provides a convenient access to precursors for the preparation of tricyclic heteroaromatic cores. The structures of 3a,b,d, 6, and 9 were confirmed by single-crystal X-ray analysis, and dibromides 3a and 3b were used for the preparation of dithieno-[2,3-b:3',2'-d]-pyrrole 10a and its selenophene analogue 10b, respectively.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/ol1006423 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Influence of biodegradable plastics on the generation of disinfection byproducts in the chlorination process.
Chemosphere
August 2024
College of Environmental Science and Engineering/Ministry of Education Key Laboratory of Pollution Processes and Environmental Criteria/Tianjin Key Laboratory of Environmental Remediation and Pollution Control, Nankai University, Tong Yan Road 38, Tianjin, 300350, China. Electronic address:
Biodegradable plastics (BPs) have seen a continuous increase in annual production and application due to their environmentally sustainable characteristics. However, research on the formation of disinfection byproducts (DBPs) from biodegradable microplastics (BMPs) during chlorination is limited, and the effects of aqueous solution chemistry on this process have yet to be explored. Therefore, two biodegradable microplastics, polylactic acid (PLA) and polybutylene adipate terephthalate (PBAT), were investigated in this study to examine the changes in their physicochemical properties before and after chlorination, and the formation of DBPs under different environmental conditions.
View Article and Find Full Text PDFDirect C-H Hydroxylation of -Heteroarenes and Benzenes Base-Catalyzed Halogen Transfer.
J Am Chem Soc
April 2024
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, United States.
Hydroxylated (hetero)arenes are valued in many industries as both key constituents of end products and diversifiable synthetic building blocks. Accordingly, the development of reactions that complement and address the limitations of existing methods for the introduction of aromatic hydroxyl groups is an important goal. To this end, we apply base-catalyzed halogen transfer (X-transfer) to enable the direct C-H hydroxylation of mildly acidic -heteroarenes and benzenes.
View Article and Find Full Text PDFSynthesis of β-Amino Acid Derivatives via Enantioselective Lewis Base Catalyzed N-Allylation of Halogenated Amides with Morita-Baylis-Hillman Carbonates.
Chemistry
March 2024
Institute for Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University Jena, Humboldtstrasse 10, 07743, Jena, Germany.
Trifluoro- and trichloroacetamides serving as pronucleophiles undergo enantioselective Lewis base catalyzed N-allylation with Morita-Baylis-Hillman carbonates to produce enantioenriched β-amino acid derivatives. The reactions proceed as a kinetic resolution to give the allylation products and the remaining carbonates in good yields and high enantioselectivity. The obtained products are amenable to diastereoselective derivatization to produce a library of spiro-isoxazoline lactams.
View Article and Find Full Text PDFBase-Catalyzed Nucleophilic Addition Reaction of Indoles with Vinylene Carbonate: An Approach to Synthesize 4-Indolyl-1,3-dioxolanones.
Molecules
November 2023
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China.
The -functionalized indole is a privileged structural framework in a wide range of bioactive molecules. The nucleophilic addition between indoles with vinylene carbonate proceeded smoothly in the presence of KCO as the catalyst to produce novel indolyl-containing skeletons and 4-indolyl-1,3-dioxolanones in satisfactory to excellent yields (up to >97% yield). Various synthetically useful functional groups, such as halogen atoms, cyano, nitro, and methoxycarbonyl groups, remained intact during the regioselective -H addition reactions.
View Article and Find Full Text PDFProduction of Dichloroacetonitrile from Derivatives of Isoxaflutole Herbicide during Water Treatment.
Environ Sci Technol
November 2023
Department of Energy, Environmental & Chemical Engineering Washington University in St. Louis, St. Louis, Missouri 63130, United States.
The herbicide isoxaflutole has the potential to contaminate drinking water directly, as well as upon hydrolyzing to its active form diketonitrile. Diketonitrile also may impact water quality by acting as a precursor for dichloroacetonitrile (DCAN), which is an unregulated but highly toxic disinfection byproduct (DBP). In this study, we investigated the reaction of diketonitrile with free chlorine and chloramine to form DCAN.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!