Enantioselective Radical Construction of 5-Membered Cyclic Sulfonamides by Metalloradical C-H Amination.

ABSTRACT: Both arylsulfonyl and alkylsulfonyl azides can be effectively activated by the cobalt(II) complexes of D₂-symmetric chiral amidoporphyrins for enantioselective radical 1,5-C-H amination to stereoselectively construct 5-membered cyclic sulfonamides. In addition to C-H bonds with varied electronic properties, the Co(II)-based metalloradical system features chemoselective amination of allylic C-H bonds and is compatible with heteroaryl groups, producing functionalized 5-membered chiral cyclic sulfonamides in high yields with high enantioselectivities. The unique profile of reactivity and selectivity of the Co(II)-catalyzed C-H amination is attributed to its underlying stepwise radical mechanism, which is supported by several lines of experimental evidence.

SUBMITTER: Hu Y 

PROVIDER: S-EPMC6854306 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature