New classes of unexplored benzo[]thiolanes are synthesized from trisubstituted thioamides through copper-catalyzed intramolecular -arylation of thioamides for the first time. This method provides good to excellent yields with fully controlled chemoselectivity. Unusually, iminobenzo[]thiolanes are very stable under mild acidic conditions. A plausible mechanism is proposed for the chemoselective -arylation process.
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http://dx.doi.org/10.1021/acsomega.1c03410 | DOI Listing |
Org Lett
October 2024
School of Chemistry, Dalian University of Technology (DUT), Dalian, 116081, China.
This study introduces an innovative copper/electric dual-catalyzed approach to Ullmann coupling reactions. Our research delineates a series of chemoselective cross-couplings among various halogenated aromatics and enantioselective couplings involving halogenated aryl aldehydes. We employed a flux screening technique to refine the reaction parameters, which is rarely reported in the field of electrochemical synthesis.
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September 2024
School of Pharmaceutical and Chemical Engineering & Institute for Advanced Studies, Taizhou University, Taizhou 318000, Zhejiang, China.
A copper-catalyzed Ullmann-type cross-coupling reaction of sulfenamides with aryl iodides is developed. The key to success is the use of a 2-methylnaphthalen-1-amine-derived amide ligand, which enables the formation of an S-C bond to access functionalized sulfilimines in good to excellent yields at room temperature. This method has the advantages of mild conditions, a broad substrate scope, good functional group compatibility, and high chemoselectivity.
View Article and Find Full Text PDFRSC Adv
March 2021
Institut de Chimie Organique et Analytique (ICOA), Université d'Orléans, UMR CNRS 7311 BP 6759 45067 Orléans Cedex 2 France
Despite the pharmacological potential of the pyrazolo[3,4-]pyrazoles, only a few methods of preparation and direct functionalization of this moiety have been described. We report herein a convenient design of new pyrazolo[3,4-]pyrazoles with a high therapeutic impact. The effective chosen strategy consists of hydrazine condensations and C-N Ullmann-type cross-coupling reactions with microwave activation.
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December 2021
Department of Biochemistry, University of Bayreuth, Universitätsstr. 30, 95440 Bayreuth, Germany.
The water-soluble quencher hydrodabcyl can be activated as an -succinimidyl ester that is readily accessible from crude hydrodabcyl and storable for a long time. With primary and secondary amines, it reacts swiftly and chemoselectively, even in the presence of other competing nucleophiles such as those typically present in natural peptides. One of the three phenolic OH groups of hydrodabcyl is amenable to selective mono-Boc protection resulting in reduced polarity, advantageous to its further use in organic synthesis.
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August 2021
School of Chemical Sciences, National Institute of Science Education and Research (NISER), Bhubaneswar HBNI, Jatni, Khurda 752050, Odisha, India.
New classes of unexplored benzo[]thiolanes are synthesized from trisubstituted thioamides through copper-catalyzed intramolecular -arylation of thioamides for the first time. This method provides good to excellent yields with fully controlled chemoselectivity. Unusually, iminobenzo[]thiolanes are very stable under mild acidic conditions.
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