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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
Published on: June 20, 2014
A Photoredox C-H Arene Functionalization toward Substituted Methyls
Jonas Žurauskas1, Nojus Radzevičius1, Paulius Vaicku̅nas1
1Department of Organic Chemistry, Vilnius University, Naugarduko 24, LT-03225 Vilnius, Lithuania.
Abstract:
The ability to introduce modular C1 units directly into arene C-H bonds remains a fundamental challenge in synthetic design, limiting access to highly diversified molecular architectures from simple feedstocks. We disclose a photoredox-neutral platform that enables direct transfer of a methylene pyridinium linchpin to unactivated arenes, transforming inert C-H sites into versatile synthetic handles. The resulting benzylpyridinium products function as broadly addressable intermediates, supporting a wide range of C-C and C-heteroatom bond formation and granting streamlined access to medicinally privileged substituted methyls.
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