Congde Huo

Catalytic Radical Cation Salt Induced Csp3–H Functionalization of Glycine Derivatives: Synthesis of Substituted Quinolines

A domino C(sp(3))-H functionalization of glycine derivatives was achieved under catalytic radical cation salt induced conditions, producing a series of quinolines. The proposed mechanism shows that a peroxyl radical cation, which is generated by the coupling between O(2) and TBPA(+•), might be involved to initiate the catalytic oxidation.

Auto-Oxidative Coupling of Glycine Derivatives†

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.

Catalytic sp3 C–H Oxidation of Peptides and Their Analogues by Radical Cation Salts: From Glycine Amides to Quinolines

A catalytic α-sp(3) 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.

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

A direct construction of quinoline-fused lactones and lactams was achieved by sp(3) 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.

Aerobic oxidative Mannich reaction promoted by catalytic amounts of stable radical cation salt.

A catalytic amount of triarylaminium salt is demonstrated to be an efficient initiator for oxidative Mannich reaction of tertiary amines and nonactivated ketones under mild neutral conditions. Air is essential for this reaction and acts as a terminal oxidant. Metal catalysts, acid or base additives, and stoichiometric amounts of chemical oxidants are all avoided in this methodology. Six examples of intramolecular cyclized products are also delivered.

Copper-Catalyzed Aerobic Oxidative Dehydrogenative Formal [2 + 3] Cyclization of Glycine Esters with α-Angelicalactone: Approach To Construct Polysubstituted Pyrrolidones

A novel and efficient copper-catalyzed aerobic oxidative dehydrogenative formal [2 + 3] cyclization of glycine derivatives with α-angelicalactone is described. A series of complex pyrrolidones were produced under mild and simple reaction conditions.

Brønsted Acid-Catalyzed Three-Component Reaction of Anilines, α-Oxoaldehydes, and α-Angelicalactone for the Synthesis of Complex Pyrrolidones

A green and efficient three-component reaction of easily available anilines, α-oxoaldehydes, and α-angelicalactone was developed for the synthesis of highly functionalized pyrrolidones using dilute sulfuric acid as the catalyst. Products were obtained in good to high yields at room temperature and under solvent-free conditions. The reaction could also be performed on a multigram scale with the same efficiency.