Silver(I)- and Base-Mediated [3 + 3]-Cycloaddition of C,N-Cyclic Azomethine Imines with Aza-oxyallyl Cations

Advances in heterocycle synthesis via [3+m]-cycloaddition reactions involving an azaoxyallyl cation as the key intermediate.

[3 + 2]-Cycloaddition of Azaoxyallyl Cations with Hexahydro-1,3,5-triazines: Access to 4-Imidazolidinones.

Synthesis of 2-Aminoimidazolones and Imidazolones by (3 + 2) Annulation of Azaoxyallyl Cations

Radical‐initiated difunctionalization of alkenes is one of the most important methods in organic synthesis and medicinal chemistry, which can be applied to synthesize value complex compounds as well as structural motifs that found in bioactive natural products and pharmaceuticals. In recent years, impressive progress have been made in this area with ideal silver catalysis. Here, we summarize recent advances in silver‐mediated radical difunctionalization of alkenes for the formation of diverse bonds, including 1) two‐component radical difunctionalization reactions enabled by an intramolecular cyclization process toward various cyclic compounds and 2) three‐component radical difunctionalization reactions leading to complex linear compounds. These silver‐mediated radical alkene difunctionalization transformations are general initiated by different radicals, such as carbon‐, oxygen‐, sulfur‐, phosphinyl‐, and halogen‐center radicals, followed by terminated with nucleophiles to form two new bonds in a single reaction.

Recent Advances in Silver-Mediated Radical Difunctionalization of Alkenes

Efficient one-pot synthesis of 1,3-dihydro-2H-pyrrol-2-one derivatives via aza-oxyallylic cations

Synthesis of thiazolidin-4-ones via [3+2] cycloaddition of in situ generated aza-oxyallylic cations with isothiocyanates

Efficient synthesis of 1,2,4-oxadiazine-5-ones via [3+3] cycloaddition of in situ generated aza-oxyallylic cations with nitrile oxides

An efficient Fe-catalyzed esterification of primary, secondary, and tertiary amides with various alcohols for the preparation of esters was performed. The esterification process was accomplished with FeCl3·6H2O, which is a stable, inexpensive, environmentally friendly catalyst with high functional group tolerance.

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Rongxing Chen

Papers

Efficient one-pot synthesis of 1,3-dihydro-2H-pyrrol-2-one derivatives via aza-oxyallylic cations

Synthesis of thiazolidin-4-ones via [3+2] cycloaddition of in situ generated aza-oxyallylic cations with isothiocyanates

Efficient synthesis of 1,2,4-oxadiazine-5-ones via [3+3] cycloaddition of in situ generated aza-oxyallylic cations with nitrile oxides

Fe-catalyzed esterification of amides via C–N bond activation

A highly diastereoselective [3+3] annulation reaction of aza-oxyallyl cations and nitrones