Rh(III)-catalyzed oxidative amidation of aldehydes: An efficient route to N-pyridinamides and imides

Copper-catalyzed highly efficient oxidative amidation of aldehydes with 2-aminopyridines in an aqueous micellar system

“…The present work offers several practical advantages such as the use of mild reaction conditions, short reaction time, the absence of base and ligand, under air, and an easy workup procedure. In addition to previously reported methods, 14,15 we demonstrated that aliphatic aldehydes were well tolerated under optimal reaction conditions. Further synthesis of a library of new diversified N-( pyridine-2-yl)amides is in progress to evaluate their biological potential.…”

“…12b,13 Recently, Huang et al 14 reported the synthesis of N-( pyridine-2-yl)amides using CuI (10 mol%) in DMF at 80 °C for 24 h (Scheme 1a). Luo et al 15 also reported the Rh(III) catalyzed synthesis of N-pyridinamides in acetone at 100 °C for 12 h (Scheme 1b). However, these methodologies suffer from several drawbacks, such as harsh reaction conditions, long reaction time, and use of hazardous solvents.…”

n‐Bu4NI/K2S2O8‐Mediated C−N Coupling Between Aldehydes and Amides

“…Recently, the Nacylation of amides by aldehydes or alcohols via cross dehydrogenative coupling has attracted great interest. The known methods include transition-metal such as copper, [6] iron, [7] rhodium, [8] or palladium, [9] and N-heterocyclic carbene (NHC) [10] catalyzed oxidative N-acylation of amides by aldehydes (Scheme 1, Eq 1) and copper [11] catalyzed oxidative N-acylation of amides by alcohols.…”

Rhodium(III)-catalyzed chelation-assisted C-H imidation of arenes via umpolung of the imidating reagent

“…Among the numerous C-H activation catalysts, Cp*Rh(III)/Ir(III) complexes have stood out as competent catalysts for directing group-assisted direct C−H functionalization with high catalytic activity, selectivity, and functional group tolerance [32][33][34][35][36][37][38][39]. So far, the Rh(III)-catalyzed C−H amination proceeded via chelation-assisted strategies include the following categories on the basis of the distinct mechanism: (1) the nitrene insertion using nitrene precursors such as organic azides, dioxazolones, anthranils, and TsNH2/PhI(OAc)2 (Scheme 1(a)) [34][35][36][37][38][39][40][41][42][43][44][45][46][47][48]61,68,69], (2) SN-type amination using an electrophilic aminating reagent (Scheme 1b) [49][50][51][52][53][54][55][56][57][58][59][60] and (3) the oxidative amination using a nucleophilic aminating re-agent (Scheme 1(c)) [70]. Although amination has been realized under redox-neutral conditions using nitrenoid reagents [40][41][42]…”