Visible-Light-Promoted Desulfurative Alkylation of Alkyl Thianthrenium Salts with Activated Olefins.
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DOI: 10.1021/acs.orglett.2c01525
Abstract: Reactions involving an alkyl radical generated from a primary alcohol by photochemistry are rare and challenging. Herein, we present a photocatalyst- and metal-free approach that enables the generation of an alkyl radical from the corresponding… read more here.
Keywords: light promoted; alkyl thianthrenium; desulfurative alkylation; thianthrenium ... See more keywords
Palladium(II)-Catalyzed Heck Coupling: Direct Stereoselective Synthesis of C-Aryl Glycosides from Nonactivated Glycals and Thianthrenium Salts.
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DOI: 10.1021/acs.orglett.4c00654
Abstract: Here, we report an efficient Pd(II)-catalyzed Heck coupling reaction utilizing modular and readily available thianthrenium salts. The tunability and ease of thianthrenium salts facilitated the integration of glycals with drugs, natural products, and peptides. This… read more here.
Keywords: thianthrenium salts; catalyzed heck; thianthrenium; aryl glycosides ... See more keywords
Photo- and Cu-Mediated 11C Cyanation of (Hetero)Aryl Thianthrenium Salts.
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DOI: 10.1021/acs.orglett.4c00929
Abstract: We present a photo- and Cu-mediated 11C cyanation of bench-stable (hetero)aryl thianthrenium salts via an aryl radical addition pathway. The thianthrenium substrates can be readily accessed via C-H functionalization, and the radiocyanation protocol proceeds under… read more here.
Keywords: mediated 11c; hetero aryl; thianthrenium; photo mediated ... See more keywords
Photoinduced Regioselective Fluorination and Vinylation of Remote C(sp3)-H Bonds Using Thianthrenium Salts.
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DOI: 10.1021/acs.orglett.4c01420
Abstract: Herein, a photoredox-driven practical protocol for fluorinated alkene synthesis using easily accessible and modular thianthrenium salts with electron-withdrawing alkynes or propargyl alcohols is reported. Vinyl radical intermediates, formed by the reaction between the alkyl or… read more here.
Keywords: photoinduced regioselective; thianthrenium; thianthrenium salts; fluorination vinylation ... See more keywords
Mechanism of Z-Selective Allylic Functionalization via Thianthrenium Salts.
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DOI: 10.1021/jacs.4c00682
Abstract: A detailed mechanistic study of the Z-selective allylic functionalization via thianthrenium salts is presented. Kinetic analyses, deuterium labeling experiments, and computational methods are used to rationalize the observed reactivity and selectivity. We find that the… read more here.
Keywords: via thianthrenium; selective allylic; thianthrenium salts; thianthrenium ... See more keywords
Palladium-catalyzed carbonylative synthesis of acrylamides from alkenyl thianthrenium salts
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DOI: 10.1039/d5sc06079f
Abstract: Covalent drugs have emerged as powerful tools in modern therapeutics, with acrylamide being one of the most widely used electrophilic warheads in recent years. Herein, we report a practical and selective strategy for synthesizing acrylamides… read more here.
Keywords: thianthrenium salts; palladium catalyzed; thianthrenium; catalyzed carbonylative ... See more keywords