Ru(ii)-Catalyzed C6-selective C–H amidation of 2-pyridones

Abstract

An efficient Ru-catalyzed C6 site-selective amidation of 2-pyridones has been accomplished with dioxazolone under mild conditions.

Beyond a solvent: triple roles of dimethylformamide in organic chemistry

“…The formation of dihydropyrrolizino[3,2-b]indol-10-ones 94 was accomplished via a Cs 2 CO 3 -promoted cascade reaction of N-tosyl-2-(2-bromophenylacetyl)pyrroles 93 with DMF in absence of any exogenous transition metal catalyst or ligand (Scheme 42). 129 A plausible mechanism for this transformation is suggested through nucleophilic attack of DMF with enolate and pyrrolyl nitrogen followed by formation of C-N bond (Scheme 43).…”

Rhodium(III)-catalyzed one-pot synthesis of flavonoids from salicylaldehydes and sulfoxonium ylides

“…Recently, sulfoxonium ylides have received wide attention 29 as safer carbene precursor. [30][31][32][33][34][35] Based on our previous research on C-H bond activation 36,37 and heterocyclic chemistry, herein we report an efficient one-pot synthesis of flavonoids via Rh(III)-catalyzed C-H bond activation and annulation of salicylaldehydes 23,27 with sulfoxonium ylides (Scheme 1(c)).…”

Rhodium(III)‐Catalyzed C−H Bond Functionalization of 2‐Pyridones with Alkynes: Switchable Alkenylation, Alkenylation/Directing Group Migration and Rollover Annulation

“…In pioneering studies, Hirano and Miura introduced an easily attachable and detachable pyridine‐based directing group (DG) on the nitrogen atom of the 2‐pyridone skeleton to facilitate C6‐selective heteroarylation of 2‐pyridones [7c] . Subsequently, transition‐metal catalyzed directed alkynylation, [6d] alkylation, [7e,h,l,u] annulation, [7f,o] borylation, [7g] arylation, [7h,k,m] thiolation, [7i] allylation, [7j] amidation [7p,q] and alkenylation [7s,t] of 1‐(2‐pyridyl)‐2‐pyridones at the C6 positions have been successfully developed. In general, the pyridyl directing group in these C−H functionalizations remains intact and can be removed from the final products.…”