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

One-Pot Synthesis of β‑Hydroxysulfones and Its Application in the Preparation of Anticancer Drug Bicalutamide

An efficient one-pot multistep strategy has been developed, comprising auto-oxidative difunctionalization of alkenes, oxidation of sulfides, and a further reduction of peroxides for the synthesis of complex β-hydroxysulfone derivatives from phenthiols and alkenes. This method has several advantageous characteristics, including readily available substrates, low-cost and environmental benign reagents, nontoxic and renewable solvents, and mild reaction conditions. The application of this transformation to the multigram-scale preparation of the anticancer drug bicalutamide is accomplished

Oxidative Dehydrogenative [2 + 3]-Cyclization of Glycine Esters with Aziridines Leading to Imidazolidines

Oxidative dehydrogenative [2 + 3]-cyclization of glycine derivatives with <i>N</i>-sulfonylaziridines is described. A series of complex imidazolidines were produced under mild and simple reaction conditions. A mechanism involving an unusual acid-promoted auto-oxidation is proposed

Iron Catalyzed Dual-Oxidative Dehydrogenative (DOD) Tandem Annulation of Glycine Derivatives with Tetrahydrofurans

A novel iron-catalyzed dual-oxidative dehydrogenative (DOD) tandem annulation of glycine derivatives with tetrahydrofurans (THFs) for the synthesis of high value quinoline fused lactones has been developed. The reactions were performed under mild reaction conditions. And the use of cheap substrates (glycine derivatives and THF) and an even cheaper simple inorganic iron salt as the catalyst makes this protocol very attractive for potential synthetic applications

CBr₄ Mediated Oxidative C–N Bond Formation: Applied in the Synthesis of Imidazo­[1,2-α]pyridines and Imidazo­[1,2-α]pyrimidines

The carbon tetrabromide mediated oxidative carbon–nitrogen bond formation of 2-aminopyridines or 2-aminopyrimidines with β-keto esters or 1,3-diones, leading to a variety of complex imidazo­[1,2-α]­pyridines or imidazo­[1,2-α]­pyrimidines, is reported. The reactions were realized under mild and metal-free conditions

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

Triphenylphosphine‑<i>m</i>‑sulfonate/Carbon Tetrabromide as an Efficient and Easily Recoverable Catalyst System for Friedel–Crafts Alkylation of Indoles with Carbonyl Compounds or Acetals

A solid complex, conveniently prepared from commercially available sodium triphenylphosphine-<i>m</i>-sulfonate (TPPMS) and carbon tetrabromide, can be used as an easily recoverable and reusable catalyst system for Friedel–Crafts alkylation of indoles with carbonyl compounds or acetals to produce bis­(indolyl)­alkane products (BIAs)

Catalytic Radical Cation Salt Induced C_sp³–H Functionalization of Glycine Derivatives: Synthesis of Substituted Quinolines

A domino C_sp³–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 O₂ and TBPA^+•, might be involved to initiate the catalytic oxidation

Approach to Construct Polysubstituted 1,2-Dihydronaphtho[2,1‑<i>b</i>]furans and Their Aerobic Oxidative Aromatization

Triarylaminium salt was disclosed as an efficient initiator for the novel Friedel–Crafts alkylation/annulation cascade reaction between chalcone epoxides and 2-naphthols to construct polysubstituted 1,2-dihydronaphtho­[2,1-<i>b</i>]­furans. The DDQ/NaNO₂/O₂ catalytic system was first applied to the aerobic oxidative aromatization of heterocycles, and a simple and efficient one-pot tandem FC alkylation/annulation/aerobic oxidative aromatization procedure was also developed for the synthesis of complex naphtho­[2,1-<i>b</i>]­furans

Approach to Construct Polysubstituted 1,2-Dihydronaphtho[2,1‑<i>b</i>]furans and Their Aerobic Oxidative Aromatization

Triarylaminium salt was disclosed as an efficient initiator for the novel Friedel–Crafts alkylation/annulation cascade reaction between chalcone epoxides and 2-naphthols to construct polysubstituted 1,2-dihydronaphtho­[2,1-<i>b</i>]­furans. The DDQ/NaNO₂/O₂ catalytic system was first applied to the aerobic oxidative aromatization of heterocycles, and a simple and efficient one-pot tandem FC alkylation/annulation/aerobic oxidative aromatization procedure was also developed for the synthesis of complex naphtho­[2,1-<i>b</i>]­furans