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Catalytic Olefin Cyclopropanation with In Situ-Generated Dialkyl Diazomethanes via Co(II)-Based Metalloradical Catalysis

Titelangaben

Cai, Bao-Gui ; Empel, Claire ; Jana, Sripati ; Xuan, Jun ; Koenigs, Rene M.:
Catalytic Olefin Cyclopropanation with In Situ-Generated Dialkyl Diazomethanes via Co(II)-Based Metalloradical Catalysis.
In: ACS Catalysis. Bd. 13 (2023) . - S. 11851-11856.
ISSN 2155-5435
DOI: https://doi.org/10.1021/acscatal.3c02468

Abstract

The synthesis of dialkyl-substituted cyclopropanes is an important challenge in synthesis with applications in drug discovery and agrochemistry. Herein, we report on the synthesis of gem-dialkyl cyclopropanes with in situ-generated dialkyl diazo compounds under Bamford–Stevens conditions. A simple cobalt catalyst was identified to be optimal to achieve high yields. Experimental and computational studies suggest the participation of a metalloradical reaction mechanism that facilitates the carbene transfer reactions and provides access to dialkyl-substituted cyclopropanes in a single step.

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Publikationsform: Artikel in einer Zeitschrift
Begutachteter Beitrag: Ja
Keywords: carbene transfer; cyclopropanation; radical chemistry; cobalt; computational chemistry
Institutionen der Universität: Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften > Fachgruppe Chemie
Titel an der UBT entstanden: Nein
Themengebiete aus DDC: 500 Naturwissenschaften und Mathematik > 540 Chemie
Eingestellt am: 28 Mär 2025 10:12
Letzte Änderung: 28 Mär 2025 10:12
URI: https://eref.uni-bayreuth.de/id/eprint/93038