This report outlines a versatile strategy for synthesizing a diverse array of N-heterocycles. By the utilization of common olefins, this simple protocol facilitates their coupling with various bifunctional reagents. Furthermore, it can be integrated with C-H amination techniques to directly produce N-heterocycles in a multicomponent cascade coupling process. The unique bond disconnection logic employed in this process underscores its efficiency in achieving rapid simplification through cascade couplings.
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http://dx.doi.org/10.1021/acs.orglett.3c03690 | DOI Listing |
J Org Chem
December 2024
College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, Zhejiang, China.
In this work, a switchable synthesis of β-ketosulfone and α-chloroketone through a radical difunctionalization of alkenes is reported. The transformation works well under iron peroxo species/photoredox dual catalysis and an open-flask atmosphere, and the reaction is highlighted with good yields and a broad reaction scope. Mechanism studies show that the reaction is initiated by a formal [4 + 2] cyclization of the sulfonyl radical in a regioselective manner.
View Article and Find Full Text PDFJ Am Chem Soc
December 2024
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China.
Chem
October 2024
Department of Chemistry, University of Chicago, Chicago, Illinois 60637, United States.
Arylethylamines represent a privileged scaffold in pharmaceutical compounds and form the backbone of many medical drugs, including those used for treating neurological diseases and pain. Their biomedical significance has inspired new synthetic methods that rely on transition metal-catalyzed aminoarylation reaction to an alkene, often in conjunction with a photoredox catalyst or a photosensitizer, and guided by a directing or stabilizing group. Here, we introduce a simple and effective method for azidoarylation of unactivated alkenes under transition metal-free conditions.
View Article and Find Full Text PDFOrg Lett
December 2024
School of Life Sciences and Medicine, Shandong University of Technology, Zibo 255000, Shandong, P. R. China.
A nickel-catalyzed intermolecular three-component 1,1-difunctionalization of unactivated alkenes with quinoxaline/naphthoquinone and arylboronic acids via organometallic-radical relay is developed. This efficient protocol provides a new method to access a variety of arylalkanes in moderate to good yields with a broad substrate scope and excellent functional group tolerance. The mechanistic studies provide insights into the mechanism and origin of chemo- and regioselectivity as well as confirm the generation of functionalized benzylic radicals.
View Article and Find Full Text PDFJ Am Chem Soc
December 2024
Department of Chemistry, Johns Hopkins University; Baltimore, Maryland 21218, United States.
The trifluoromethyl (-CF) group represents a highly prevalent functionality in pharmaceuticals. Over the past few decades, significant advances have been made in the development of synthetic methods for trifluoromethylation. In contrast, there are currently no metalloenzymes known to catalyze the formation of C(sp)-CF bonds.
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