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

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 beta-amino acids. Characterized by mild conditions and wide scope of migrating species, this protocol allows the modular assembly of sp(3)-aryls under transition metal-free, room-temperature conditions.

Automated summary

The ring-opening of 3-aminocyclobutanone oximes leads to the formation of primary alkyl radicals, enabling a novel strain-release, desulfonylative radical Truce-Smiles rearrangement process, which allows for the divergent synthesis of valuable 1,3 diamines and unnatural beta-amino acids. The protocol is characterized by mild conditions and a wide range of migrating species, facilitating the modular assembly of sp(3)-aryls under transition metal-free, room-temperature conditions.