Rhodium-Catalyzed Direct C7 Alkynylation of Indolines

An efficient rhodium(III)‐catalyzed direct C7 alkynylation of indoline CH bonds with the alkynylated hypervalent iodine reagents has been developed. This reaction proceeds smoothly under mild conditions over a wide structural scope with high site‐selectivity and excellent functional‐group tolerance...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2015-04, Vol.357 (6), p.1149-1153
Main Authors: Jin, Ning, Pan, Changduo, Zhang, Honglin, Xu, Pan, Cheng, Yixiang, Zhu, Chengjian
Format: Article
Language:English
Subjects:
alkynylation
Catalysis
CH activation
Indoles
indolines
Iodine
rhodium
Synthesis
Tolerances
Transformations
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Summary:An efficient rhodium(III)‐catalyzed direct C7 alkynylation of indoline CH bonds with the alkynylated hypervalent iodine reagents has been developed. This reaction proceeds smoothly under mild conditions over a wide structural scope with high site‐selectivity and excellent functional‐group tolerance. N‐Acetyl as well as other N‐acyls served as effective directing groups (DG). This procedure allows for the synthesis of a variety of 7‐alkynyl‐substituted indolines in good to excellent yield. More significantly, C7‐alkynylated indoles through further transformations have been successfully accessed.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201401007