American Chemical Society
ja2c08304_si_001.pdf (25.75 MB)

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

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journal contribution
posted on 2022-09-15, 17:47 authored by Changcheng Jing, Benjamin T. Jones, Ross J. Adams, John F. Bower
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.