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Enantioselective Intramolecular C–H Alkylation Catalyzed by a Nonsymmetric Chiral Cobalt Porphyrin

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide Upon catalysis (1 mol %) by a chiral cobalt porphyrin, quinazolinones with a tethered diazo alkane precursor underwent an enantioselective C–H alkylation at carbon atom C4. Formation of five-, six-, and seven-membered rings was successfully accomplished (27 examples, 72–99% yield, 47–99% ee ). Experimental and computational studies suggest that the catalyst recruits the substrates by two-point hydrogen bonding. After formation of a cobalt-entangled carbon-centered radical, a sequence of hydrogen abstraction and homolytic substitution is precisely orchestrated by the chiral confinement of the cobalt porphyrin.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.5c19047

Authors: Christoph Buchelt, Stefan Breitenlechner, Julian Zuber, Stefan M. Huber, Thorsten Bach

Institutions: Technical University of Munich, Ruhr University Bochum

Language: English

Topic: Cyclopropane Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Fonds der Chemischen Industrie, Deutsche Forschungsgemeinschaft