Direct synthesis of aryl-annulated [c]carbazoles by gold(i)-catalysed cascade reaction of azide-diynes and arenes. Issue 44 (18th September 2018)

• Record Type: Journal Article
• Authors: Kawada, Yuiki; Ohmura, Shunsuke; Kobayashi, Misaki; Nojo, Wataru; Kondo, Masaki; Matsuda, Yuka; Matsuoka, Junpei; Inuki, Shinsuke; Oishi, Shinya; Wang, Chao; Saito, Tatsuo; Uchiyama, Masanobu; Suzuki, Takanori; Ohno, Hiroaki
• Is Part Of: Chemical science. Volume 9:Issue 44(2018)
• Page Start: 8416
• Page End: 8425
• Publication Date: 2018-09-18
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c8sc03525c
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : The gold-catalysed annulation of conjugated alkynes bearing an azido group with arenes gave annulated [ c ]carbazoles. Abstract : The gold-catalysed annulation of conjugated alkynes bearing an azido group with arenes gave annulated [ c ]carbazoles. Using benzene, pyrrole, and indole derivatives as the nucleophiles, benzo[ c ]-, pyrrolo[2, 3- c ]-, and indolo[2, 3- c ]carbazoles were produced, respectively. The reaction proceeded through pyrrole and benzene ring construction accompanied by the formation of two carbon–carbon and one carbon–nitrogen bond and the cleavage of two aromatic C–H bonds. The mechanism of the reaction with pyrrole was investigated by density functional theory calculations. N, N ′-dimethylated indolo[2, 3- c ]carbazole showed dual ultraviolet-visible-near-infrared and fluorescence spectral changes upon electrolysis.