We report, herein, a photoinduced iron-catalyzed direct chlorination of aromatic sulfonyl chloride at room temperature. In this protocol, FeCl-catalyzed direct chlorination has been realized at room temperature under the irradiation of light (400-410 nm). During the process, many commercially or readily available substituted aromatic sulfonyl chlorides could produce the corresponding aromatic chlorides in moderate to good yields.
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http://dx.doi.org/10.1021/acs.orglett.3c01642 | DOI Listing |
J Org Chem
December 2024
Key Laboratory of Advanced Materials Technologies, International (Hong Kong Macao and Taiwan) Joint Laboratory on Advanced Materials Technologies, College of Materials Science and Engineering, Fuzhou University, Fuzhou, Fujian 350108, China.
The structure-activity relationship between the metal center and regio-selectivity is persistently a pivotal scientific issue. To address this, we select the 2-phenylpyridine sulfonylation reactions catalyzed by ruthenium and palladium as research subjects. An extensive theoretical study has been conducted on their reaction mechanisms, the sources of regio-selectivity, and the evolution of electronic structures.
View Article and Find Full Text PDFOrg Lett
December 2024
School of Medicine, Huaqiao University, Quanzhou 362021, P. R. China.
Nitrogen central radicals (NCRs) are versatile synthetic intermediates for creating functional nitrogen-containing molecules. Herein, a photosensitized β-sulfonylamination of terminal alkynes as well as acetylene has been established by employing -sulfonyl heteroaromatics as bifunctional reagents (BFRs) to efficiently deliver versatile ()-β-sulfonylvinylamines with excellent regio- and stereoselectivities. Mechanistic studies suggest a base-accelerated energy transfer (EnT) photocatalysis involving aromatic NCR formation, radical addition to alkynes, and sulfonylation processes.
View Article and Find Full Text PDFJ Org Chem
December 2024
Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur 741246 West Bengal, India.
This study presents a greener approach to the visible-light-induced micellar-catalyzed diastereoselective iodosulfonylation of cyclopropenes in a water medium. Remarkably, this process operates without a photocatalyst. Instead, it utilizes an electron-donor-acceptor complex formed between sulfonyl chloride and sodium iodide.
View Article and Find Full Text PDFJ Org Chem
December 2024
Department of Chemistry, School of Chemistry, Xi'an Key Laboratory of Sustainable Energy Material Chemistry and Engineering Research Center of Energy Storage Materials and Devices, Ministry of Education, Xi'an Jiaotong University, Xi'an 710049, China.
A catalyst-free photoinduced deconstructive fluorosulfonylation cascade of spiro dihydroquinazolinones with DABSO and NFSI is reported. This protocol features mild reaction conditions, good yields and excellent functional group tolerance, providing a practical approach to the quinazolin-4(1)-one-functionalized aliphatic sulfonyl fluorides. In addition, the ease of gram-scale synthesis and the versatility of the SuFEx exchange highlight the application potential of this protocol.
View Article and Find Full Text PDFJ Mater Chem B
November 2024
Key Laboratory of Green Chemistry and Technology (Ministry of Education), College of Chemistry, Sichuan University, Chengdu 610064, P. R. China.
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