4.8 Article

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

Journal

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.2c08304

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Funding

  1. European Research Council [639594]
  2. Leverhulme Trust (Philip Leverhulme Prize)
  3. EPSRC [EP/N509619/1]
  4. University of Liverpool
  5. European Research Council (ERC) [639594] Funding Source: European Research Council (ERC)

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Unique examples of aza-Heck-based C(sp3)-H functionalization cascades are described, where alkyl-Pd(II) intermediates generated from the aza-Heck-type cyclization of N-(pentafluorobenzoyloxy)carbamates undergo C(sp(3))-H palladation to form cyclopropanes. The key factors controlling the site selectivity of the cyclopropanation process have been elucidated, enabling selective access to a wide range of ring- or spiro-fused systems.
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(sp(3))-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.

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