A novel method for the construction of allyl arylsulfone derivatives was developed by palladium catalyzed allylation of sulfonyl hydrazides with alkynes. A series of structurally diverse allyl arylsulfones can be regioselectively synthesized in high yields under mild conditions.
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http://dx.doi.org/10.1039/c6ob01929c | DOI Listing |
Angew Chem Int Ed Engl
January 2025
Department of Chemistry, University of Illinois Chicago 845 West Taylor Street, Chicago, 60607, Illinois, USA.
Electrochemical reduction of 2-allyl-substituted nitroarenes using a simple, undivided electrochemical cell with non-precious electrodes to generate nitroarene radical anions was developed. The nitroarene radical anion intermediates participate in 1,5-hydrogen atom transfer reactions to construct quinoline N-oxides bearing aryl-, heteroaryl-, alkenyl-, benzyl-, sulfonyl-, or carboxyl groups.
View Article and Find Full Text PDFChem Sci
October 2024
Equipe Synthèse Organique et Phytochimie, Institut de Chimie, CNRS-UdS UMR 7177, 4 rue Blaise Pascal, CS 90032 67081 Strasbourg France
Herein, we report the first visible-light-induced strategy for the rapid synthesis of densely functionalized α- and γ-phosphorylated β-sulfonyl enamines in a regio- and stereoselective manner from -sulfonyl allenamides and H-phosphine oxides. The transformation displays a broad substrate scope, while operating at room temperature under photocatalyst- and additive-free conditions. In this atom-economical process, either terminal or substituted -sulfonyl allenamides trigger an unprecedented -to- [1,3]-sulfonyl shift, relying on a dual radical allyl resonance and α-heteroatom effect in its triplet excited state.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
Department of Chemistry and Biochemistry, The University of Texas at Dallas, 800 West Campbell Road, Richardson, Texas, 75080-3021, United States.
Allylic sulfones are valuable motifs due to their medicinal and biological significance and their versatile chemical reactivities. While direct allylic C-H sulfonylation represents a straightforward and desirable approach, these methods are primarily restricted to terminal alkenes, leaving the engagement of the internal counterparts a formidable challenge. Herein we report a photocatalytic approach that accommodates both cyclic and acyclic internal alkenes with diverse substitution patterns and electronic properties.
View Article and Find Full Text PDFOrg Biomol Chem
September 2024
State Key Laboratory of Silicate Materials for Architectures; and School of Chemistry, Chemical Engineering and Life Sciences, Wuhan University of Technology, Wuhan 430070, China.
A practical and efficient method for the C-3 site selective alkenylation of indoles was developed for constructing novel indole-functionalized vinyl sulfonyl fluorides and indolyl allylic sulfonyl fluorides. The reaction is accomplished with exclusive regio- and stereoselectivity without using transition metal catalysts, providing novel products of great potential value in medicinal chemistry, chemical biology, and drug discovery.
View Article and Find Full Text PDFJ Org Chem
July 2024
College of Chemistry and Chemical Engineering, Green Catalysis & Synthesis Key Laboratory of Xinyang City, Xinyang Normal University, Xinyang, Henan 464000, China.
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