4.8 Article

Interception of Cobalt-Based Carbene Radicals with α-Aminoalkyl Radicals: A Tandem Reaction for the Construction of β-Ester-γ-amino Ketones

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 4, Pages 1231-1235

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201408874

Keywords

carbene radicals; cobalt; Kornblum-DeLaMare reaction; radical reactions; tandem reactions

Funding

  1. Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD)
  2. Natural Science Foundation of China [21272165]

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The interception of cobalt-based carbene radicals with -aminoalkyl radicals was combined with the Kornblum-DeLaMare reaction and provides -ester--amino ketones, which are otherwise difficult to obtain in high chemoselectivity. Mechanistically, this transformation is an interplay of cobalt-based carbene radicals, organoradicals, and ionic intermediates and involves the construction of two CC bonds and one CO bond in a one-pot process. The reaction also features a wide substrate scope and is highly efficient and insensitive to moisture and air.

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