Net-1,2-Hydrogen Atom Transfer of Amidyl Radicals: Toward the Synthesis of 1,2-Diamine Derivatives.

ABSTRACT: Hydrogen atom transfer (HAT) processes are among the most useful approaches for the selective construction of C(sp³)-C(sp³) bonds. 1,5-HAT with heteroatom-centered radicals (O^•, N^•) have been well established and are favored relative to other 1,n-HAT processes. In comparison, net 1,2-HAT processes have been observed infrequently. Herein, the first amidyl radicalls are reported that preferentially undergo a net 1,2-HAT over 1,5-HAT. Beginning with single electron transfer from 2-azaallyl anions to N-alkyl N-aryloxy amides, the latter generate amidyl radicals. The amidyl radical undergoes a net-1,2-HAT to generate a C-centered radical that participates in an intermolecular radical-radical coupling with the 2-azaallyl radical to

SUBMITTER: Jiang Y 

PROVIDER: S-EPMC10411589 | biostudies-literature | 2023 Jul

REPOSITORIES: biostudies-literature