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Truce-Smiles Rearrangements by Strain Release: Harnessing Primary Alkyl Radicals for Metal-Free Arylation.

David M WhalleyJayasree SeayadMichael F Greaney
Published in: Angewandte Chemie (International ed. in English) (2021)
The ring-opening of 3-aminocyclobutanone oximes enables easy generation of primary alkyl radicals, capable of undergoing an unprecedented strain-release, desulfonylative radical Truce-Smiles rearrangement, providing divergent access to valuable 1,3 diamines and unnatural β-amino acids. Characterized by mild conditions and wide scope of migrating species, this protocol allows the modular assembly of sp3 -aryls under transition metal-free, room-temperature conditions.
Keyphrases
  • room temperature
  • ionic liquid
  • amino acid
  • randomized controlled trial