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Cyclopropane-Fused N-Heterocycles via Aza-Heck-Triggered C(sp3)-H Functionalization Cascades. 2022

Changcheng Jing, and Benjamin T Jones, and Ross J Adams, and John F Bower
Department of Chemistry, University of Liverpool, Crown Street, Liverpool L69 7ZD, United Kingdom.

Unique examples of aza-Heck-based C(sp3)-H functionalization cascades are described. Under Pd(0)-catalyzed conditions, the aza-Heck-type cyclization of N-(pentafluorobenzoyloxy)carbamates generates alkyl-Pd(II) intermediates that effect C(sp3)-H palladation en route to cyclopropanes. Key factors that control the site selectivity of the cyclopropanation process have been elucidated such that selective access to a wide range of ring- or spiro-fused systems can be achieved.

UI MeSH Term Description Entries
D002219 Carbamates Derivatives of carbamic acid, H2NC( Carbamate,Aminoformic Acids,Carbamic Acids,Acids, Aminoformic,Acids, Carbamic
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D003500 Cyclization Changing an open-chain hydrocarbon to a closed ring. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Cyclizations
D003521 Cyclopropanes Three-carbon cycloparaffin cyclopropane (the structural formula (CH2)3) and its derivatives.

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