1185863-95-9Relevant academic research and scientific papers
Rhodium(III)-Catalyzed Oxidative Coupling of N-Phenylindole-3-carboxylic Acids with Alkenes and Alkynes via C4-H and C2-H/C2′-H Bond Cleavage
Okada, Takeshi,Sakai, Asumi,Hinoue, Tomoaki,Satoh, Tetsuya,Hayashi, Yoshihiro,Kawauchi, Susumu,Chandrababunaidu, Kona,Miura, Masahiro
, p. 5639 - 5649 (2018/05/14)
The rhodium(III)-catalyzed direct alkenylation of N-phenylindole-3-carboxylic acids with alkenes including acrylate ester, acrylamide, and acrylonitrile proceeds smoothly at the C4-position through regioselective C-H bond cleavage directed by the carboxyl group. In marked contrast, the indole substrates react with diarylacetylenes accompanied by cleavage of the C2-H and C2′-H bonds and decarboxylation to produce 5,6-diarylindolo[1,2-a]quinolone derivatives. DFT calculations have suggested that the smooth insertion of an alkene to a C4-rhodated six-membered metallacycle intermediate leads to the C4 alkenylated products, while the latter annulation at the C2- and C2′-positions is attributable to facile reductive elimination in the corresponding seven-membered metallacycles formed by the double C-H bond cleavage and alkyne insertion.
Fused ring construction around pyrrole, indole, and related compounds via palladium-catalyzed oxidative coupling with alkynes
Yamashita, Mana,Horiguchi, Hakaru,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
scheme or table, p. 7481 - 7488 (2010/01/06)
(Chemical Equation Presented) The selective synthesis of 1,2,3,4-tetrasubstituted carbazoles can be performed effectively through the palladium-catalyzed oxidative coupling reactions of N-substituted indoles or their carboxylic acid derivatives with alkyn
