cs6b02015_si_001.pdf (4.22 MB)
Chelation-Assisted Rhodium-Catalyzed Direct Amidation with Amidobenziodoxolones: C(sp2)–H, C(sp3)–H, and Late-Stage Functionalizations
journal contributionposted on 2016-08-03, 00:00 authored by Xu-Hong Hu, Xiao-Fei Yang, Teck-Peng Loh
Air-stable and convenient amidobenziodoxolones as an amidating reagent were disclosed to enable direct amidation on a wide range of C(sp2)–H bonds of (hetero)arenes and alkenes, as well as unactivated C(sp3)–H bonds under RhIII catalysis. The approach to access 49 examples of structurally diverse amides is featured by mild conditions, complete chemoselectivity and regioselectivity, broad substrate scope (not limited to strongly heterocyclic coordinating groups), and tolerance of valuable functional substituents, such as unprotected amine and hydroxyl groups. The synthetic applicability of this protocol is also demonstrated by late-stage functionalization of biologically important scaffolds.
amineamidating reagentalkenechemoselectivityapplicabilityFunctionalizationAmidationregioselectivitysubstrate scopeheteroscaffoldfunctionalizationamidationaccess 49 examplessubstituentAmidobenziodoxolonehydroxyl groupsunactivatedamideapproachheterocyclicamidobenziodoxolonetoleranceRh III catalysisbond