Ag(I)-Catalyzed Addition of Cyclopropenones and Nitrones to Access Imides

Abstract

An unprecedented Ag-catalyzed addition reaction of cyclopropenones and nitrones to access imides was developed. Sequential C−C bond cleavage, N−O bond cleavage, and Mumm rearrangement were uncovered in this process. This protocol exhibited high efficiency, regioselectivity, good yields, and a broad tolerance of various functional groups.

Solvent-controlled amidation of acid chlorides at room temperature: new route to access aromatic primary amides and imides amenable for late-stage functionalization

“…21 Recently, considerable effort has been devoted to the synthesis of imides, and in this regard several methods have been developed, such as the metal-catalyzed carbonylation of amides, 22 the oxidation of amides, 23 and the oxidative decarboxylation of amino acids, 24 among others. [25][26][27][28][29][30][31][32][33] Recently, the Liang group reported the synthesis of imides by the chemoselective acylation of N-acylglutarimides with N-acylpyrroles and aryl esters under transition-metal-free conditions. 21 However, the reported imide synthesis displays certain drawbacks in terms of corrosive precursors, prefunctionalized substrates, specialized reagents, and excessive oxidants; besides, they are time-consuming with a limited substrate scope.…”

M-CPOnes: Transition Metal Complexes with Cyclopropenone-Based Ligands for Light-Triggered Carbon Monoxide Release

“…[22][23][24] While cyclopropenones 25,26 undergo efficient photolysis 27,28 upon irradiation with light resulting in carbon monoxide release and alkyne formation, they have been largely overlooked as CORMs. 16 Instead, cyclopropenones have found use across different fields from organic chemistry (as substrates in annulations, [29][30][31][32][33] metal-catalysed ringopening reactions, 34 cycloaddition reactions 35,36 and allene syntheses 37,38 as well as catalysts for nucleophilic substitutions 39,40 ) to material science 18,41,42 and biorthogonal chemistry. [43][44][45][46][47][48] Cyclopropenones are appealing as prospective CORMs not only for their efficient photodecarbonylation but since they can be prepared via various synthetic methods (e.g.…”

M-CPOnes: transition metal complexes with cyclopropenone-based ligands for light-triggered carbon monoxide release

“…[22][23][24] While cyclopropenones 25,26 undergo efficient photolysis 27,28 upon irradiation with light resulting in carbon monoxide release and alkyne formation, they have been largely overlooked as CORMs. 16 Instead, cyclopropenones have found use across different fields from organic chemistry (as substrates in annulations, [29][30][31][32][33] metal-catalysed ring-opening reactions, 34 cycloaddition reactions 35,36 and allene syntheses 37,38 as well as catalysts for nucleophilic substitutions 39,40 ) to material science 18,41,42 and biorthogonal chemistry. [43][44][45][46][47][48] Cyclopropenones are appealing as prospective CORMs not only for their efficient photodecarbonylation but since they can be prepared via various synthetic methods (e.g.…”