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 contribution
posted on 2016-08-03, 00:00 authored by Xu-Hong Hu, Xiao-Fei Yang, Teck-Peng LohAir-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.
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amineamidating reagentalkenechemoselectivityapplicabilityFunctionalizationAmidationregioselectivitysubstrate scopeheteroscaffoldfunctionalizationamidationaccess 49 examplessubstituentAmidobenziodoxolonehydroxyl groupsunactivatedamideapproachheterocyclicamidobenziodoxolonetoleranceRh III catalysisbond