A novel tandem SET/radical ring-opening/coupling between 2-azaallyl anions and O-aryl oxime ethers provides aminoalkyl nitriles under mild conditions. The gram-scale sequential synthesis and hydrolysis demonstrated the scalability of the chemistry.
A novel tandem radical cyclization/intermolecular coupling between 2-azaallyl anions and indole N-aryloxy acetamides is developed, which enables the synthesis of C3a-substituted pyrroloindolines under mild conditions.
A transition-metal-free C(sp3)–C(sp2) cross-coupling approach to prepare branched allylamines and azaarylmethylamines is presented. Key to the process is the enhanced reactivity of the 2-azaallyl anions generated from N-fluorenyl alkylimines.
Acyl oxyallenes are introduced as in situ precursors to α,β-unsaturated ketones for Giese radical addition with 2-azaallyl radicals. This metal-free protocol delivers diverse γ-amino ketones in high yields with broad functional-group tolerance.
Visible-light-driven N-centered radicals lead to C-centered α-amino radicals through rare net-1,2-HAT processes, with trapping by silyl enol ethers to access β-amido ketone derivatives.