Multi-site cyclization via initial C-H activation using a rhodium(III) catalyst: rapid assembly of frameworks containing indoles and indolines

Tandem multi-site cyclization triggered by Rh(iii)-catalyzed C-H activation has been achieved for highly efficient synthesis of spirocycle indolin-3-one (C2-cyclization), benzo[a]carbazole (C3-cyclization) and an unusual indoxyl core (N1-cyclization). In particular, the synthesis of pseudo-indoxyl i...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2015-02, Vol.51 (14), p.2844-2847
Main Authors: Huang, Ji-Rong, Qin, Liu, Zhu, Yu-Qin, Song, Qiang, Dong, Lin
Format: Article
Language:English
Subjects:
Carbon - chemistry
Catalysis
Cyclization
Hydrogen - chemistry
Indoles - chemistry
Kinetics
Oxidation-Reduction
Rhodium - chemistry
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Summary:Tandem multi-site cyclization triggered by Rh(iii)-catalyzed C-H activation has been achieved for highly efficient synthesis of spirocycle indolin-3-one (C2-cyclization), benzo[a]carbazole (C3-cyclization) and an unusual indoxyl core (N1-cyclization). In particular, the synthesis of pseudo-indoxyl is typically completed within 10 min, and the reaction tolerates air, water and a range of solvents.
ISSN:1359-7345
1364-548X
DOI:10.1039/c4cc07125e