A direct thionation procedure allows conversion of allylic alcohols into the corresponding thiols, the products of which are immediately compatible with one-pot site-selective selenenyl sulfide mediated protein conjugation.
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Photoredox-Catalyzed Site-Selective Intermolecular C(sp)-H Alkylation of Tetrahydrofurfuryl Alcohol Derivatives.
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Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan.
4'-Selective alkylation of nucleosides has been recognized as one of the ideal and straightforward approaches to chemically modified nucleosides, but such a transformation has been scarce and less explored. In this Letter, we combine a visible-light-mediated photoredox catalysis and hydrogen atom transfer (HAT) auxiliary to achieve β-C(sp)-H alkylation of alcohol on tetrahydrofurfuryl alcohol scaffolds and exploit it for 4'-selective alkylation of nucleosides. The reaction involves an intramolecular 1,5-HAT process and stereocontrolled Giese addition of the resultant radicals.
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Georgia State University, Chemistry, 50 Decatur ST SE, 30303, Atlanta, UNITED STATES OF AMERICA.
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Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology, School of Chemistry and Chemical Engineering, Guangxi University, Nanning, Guangxi 530004, China.
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Nat Commun
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