Aryne formation via the hexadehydro Diels-Alder reaction and their Ritter-type transformations catalyzed by a cationic silver complex. Issue 29 (20th July 2017)

• Record Type: Journal Article
• Authors: Ghorai, Sourav; Lee, Daesung
• Is Part Of: Tetrahedron. Volume 73:Issue 29(2017)
• Page Start: 4062
• Page End: 4069
• Publication Date: 2017-07-20
• Subjects: Aryne -- Aryne-silver complex -- Nitrilium ion -- Ritter reaction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.02.008
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Despite their electrophilic nature, arynes are not known to react with nitriles under typical conditions for their formation. We demonstrated, however, that structurally diverse arynes could be generated via the hexadehydro Diels-Alder reaction and trapped with nitriles to induce the Ritter-type reaction when catalyzed by a cationic silver species. Presumably, under these conditions, the transiently formed aryne-silver complexes react with nitriles initially to form nitrilium ion intermediates, which then subsequently react with either water or carboxylic acid to yield the observed arylamides or arylimides. Graphical abstract: