Benzannulated Bicycles by Three‐Component Aryne Reactions

Transition-Metal-Free Synthesis of Benzo-Fused Five- and Six-Membered Heterocycles Employing Arynes

“…A similar type of reaction with esters and electron-deficient alkynes as the third component, instead of aldehydes/ ketones/imines, has been developed by Stoltz and coworkers [66]. The MCR involving arynes, isocyanides, and phenyl esters in the presence of TBAT in THF at 40 °C resulted in the formation of the unusual phenoxy iminoisobenzofuran derivatives in good yield (Scheme 42).…”

4.09 Nucleophilic Coupling with Arynes

“…223 As shown in Scheme 71, an initially formed zwitterion 82 from an aryne and an isocyanide reacts with an aldehyde to afford intermediate 83, which is finally converted into the product by an intramolecular cyclization. Aldehydes can be replaced by ketones, 224 benzoquinones, 224 sulfonylimines, 225 esters 226 and electron-deficient alkynes, 226 …”

Aryne‐Induced Novel Tandem 1,2‐Addition/(3+2) Cycloaddition to Generate Imidazolidines and Pyrrolidines

“…[12,13] This novel strategy with effectiveness and efficiency could also be extended to the synthesis of pyrrolidines by replacement of the second equivalent of the Schiff bases with various electron-deficient alkenes. [12,13] This novel strategy with effectiveness and efficiency could also be extended to the synthesis of pyrrolidines by replacement of the second equivalent of the Schiff bases with various electron-deficient alkenes.…”