Tao Zhou, Bin Li, Baiquan Wang
Jun 8, 2017
Citations
0
Influential Citations
40
Citations
Journal
Chemical communications
Abstract
Rhodium-catalyzed oxidative annulation reactions of 3-(1H-indol-3-yl)-3-oxopropanenitriles with internal alkynes have been developed. A series of substituted carbazoles and 4H-oxepino[2,3,4,5-def]carbazoles, through a formal Rh(iii)-catalyzed (4+2) cycloaddition with an alkyne and tandem (4+2) and (5+2) cycloaddition with two molecules of alkynes, were obtained. The reactions involved sequential cleavage of C(sp2)-H/C(sp3)-H bonds and annulation with an alkyne in the first step, and sequential cleavage of C(sp2)-H/O-H bonds and annulation with another alkyne in the second step. Some of the 4H-oxepino[2,3,4,5-def]carbazole products exhibit intense fluorescence in the solid state.