Synthesis of heterocyclic compounds through nucleophilic phosphine catalysis

The stereoselective phosphine-catalyzed ((pMeOC6H4)3P, 10–20 mol %) dearomatization of 3-NO2-indoles with allenoates is described. A range of densely functionalized indolines (18 examples) is obtai...

Phosphine-Catalyzed Stereoselective Dearomatization of 3-NO2-Indoles with Allenoates.

Ytterbium and silver co-catalyzed synthesis of pyrrole-fused bicyclic skeletons from enynones and isocyanides.

Catalytic Three-Component Synthesis of Functionalized Naphtho[2,1-b]oxecines via a Double Bond Cleavage-Rearrangement Cascade.

The first [4 + 2] cyclization of para-quinone methide (p-QM) derivatives with allenes has been established via phosphine catalysis, which afforded a series of chroman derivatives in high yields (up to 97%) and excellent (E/Z)-selectivities (all >95 : 5 E/Z). This reaction will not only enrich the research contents of cyclization reactions involving p-QM derivatives, but also provide a good example of the application of allenes and phosphine catalysis in cyclization reactions. In addition, this approach also offers a useful method for the construction of chroman scaffolds.

Phosphine-catalyzed [4 + 2] cyclization of para-quinone methide derivatives with allenes.

Iron-Catalyzed Aerobic Oxidation and Annulation Reaction of Pyridine and α-Substituted Allenoate toward Functionalized Indolizine

Phosphine‐Catalyzed Domino Reaction of α,β‐Unsaturated Ketone and Allenoate: Stereoselective Synthesis of Polysubstituted Dihydro‐2H‐Pyran

A novel oxidative esterification of 1-arylprop-2-en-1-ols with toluene derivatives catalyzed by tetrabutylammonium iodide (TBAI) is reported. The optimization of the reaction conditions illustrates that each of experiment parameters including the catalyst, solvent, and oxidant is significant for present oxidative functionalization. This metal-free protocol has a broad substrate scope including the halogen groups for further functionalization and enriches the reactivity profile of allyl alcohol and toluene derivatives. In addition, this protocol represents a new transformation of allyl alcohol involving C–C bond cleavage and C–O bond forming.

Yaoyao Chen

Papers

Iron-Catalyzed Aerobic Oxidation and Annulation Reaction of Pyridine and α-Substituted Allenoate toward Functionalized Indolizine

Phosphine‐Catalyzed Domino Reaction of α,β‐Unsaturated Ketone and Allenoate: Stereoselective Synthesis of Polysubstituted Dihydro‐2H‐Pyran

Bu4NI-Catalyzed C–C Bond Cleavage and Oxidative Esteriﬁcation of Allyl Alcohols with Toluene Derivatives