https://pubs.rsc.org/en/content/articlepdf/2014/cc/c3cc47081d

Aerobic oxidation catalysis with stable radicals

The unprecedented title reaction between glycine derivatives and indoles, as well as the auto-oxidative Povarov/aromatization tandem reaction of glycine derivatives with olefins are described. The reactions were performed in the absence of redox-active catalysts and chemical oxidants under mild reaction conditions. Only simple organic solvents and air (or O2) were required.

Auto-Oxidative Coupling of Glycine Derivatives†

Visible-light-promoted and one-pot synthesis of phenanthridines and quinolines from aldehydes and O-acyl hydroxylamine.

A sustainable C-C bond formation is merged with the catalytic asymmetric generation of one or two stereocenters. The introduced catalytic asymmetric cross-coupling of two C(sp3)-H groups with molecular oxygen as the oxidant profits from the oxidative robustness of a chiral-at-metal rhodium(III) catalyst and exploits an autoxidation mechanism or visible-light photosensitized oxidation. In the latter case, the catalyst serves a dual function, namely as a chiral Lewis acid for catalyzing enantioselective enolate chemistry and at the same time as a visible-light-driven photoredox catalyst.

Aerobic Asymmetric Dehydrogenative Cross‐Coupling between Two C sp 3H Groups Catalyzed by a Chiral‐at‐Metal Rhodium Complex

The organic nitroxyl radical, TEMPO (2,2,6,6-tetramethylpiperidine-N-oxyl), finds a variety of industrial applications for chemical transformations. Because of economic and environmental concerns, ...

TEMPO in Chemical Transformations: From Homogeneous to Heterogeneous

A catalytic α-sp3 C–H oxidation of peptides and glycine amides was achieved under radical cation salt catalysis in the presence of O2, producing a series of substituted quinolines. The scope of this reaction shows good functional group tolerance and high efficiency of the oxidative functionalization.

Catalytic sp3 C-H oxidation of peptides and their analogues by radical cation salts: from glycine amides to quinolines.

A direct construction of quinoline-fused lactones and lactams was achieved by sp3 C–H bond oxidation of N-aryl glycine esters and amides under catalytic radical cation salt-induced conditions. These polycyclic products are formed in a single step from readily accessible starting materials, and this method provides a new synthetic approach to this class of heterocycles.

Radical Cation Salt-Promoted Catalytic Aerobic sp3 C–H Oxidation: Construction of Quinoline-Fused Lactones and Lactams

Cerium(IV)-Catalyzed sp3 CH Bond Oxidation of Glycine Derivatives: Radical Cation Prompted Dioxygen Activation in the Presence of Triarylamine

The formation of 1,4-dihydropyridines from glycine ester and 1,3-dicarbonyl compounds proceeds under mild conditions via radical cation salt promoted C(sp3)-H oxidation/C-N bond cleavage.

Yaxin Wang

Papers

Catalytic sp3 C-H oxidation of peptides and their analogues by radical cation salts: from glycine amides to quinolines.

Radical Cation Salt-Promoted Catalytic Aerobic sp3 C–H Oxidation: Construction of Quinoline-Fused Lactones and Lactams

Cerium(IV)-Catalyzed sp3 CH Bond Oxidation of Glycine Derivatives: Radical Cation Prompted Dioxygen Activation in the Presence of Triarylamine

Catalytic Oxidation of C(sp3) ? H Bonds Induced by a Radical Cation Salt: Construction of 1,4‐Dihydropyridines Using a Fragment‐Reassembly Strategy

Synthesis of 2,3-disubstituted quinolines from in situ generated imines and its enamine tautomer under radical cation induced conditions