Directing‐Group‐Free C7‐Alkylations of N‐Alkylindoles Mediated by Cationic Zirconium Complexes: Role of Brønsted Acid for Catalytic Manifold

Highly position selective alkylations of N‐alkylindoles at C7‐positions have been enabled by cationic zirconium complexes. The strategy provides a straightforward access to install alkyl groups at C7‐positions of indoles without a complex directing group. Mechanistic studies provided support for the...

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Bibliographic Details
Published in:Chemistry : a European journal 2019-05, Vol.25 (30), p.7292-7297
Main Authors: Chen, Ping, Hao, Yanhong, Wang, Xinxin, Yuan, Dan, Yao, Yingming, Ackermann, Lutz
Format: Article
Language:English
Subjects:
Acids
Alkylation
C7-alkylation
Catalysis
Cations
Chemistry
C−H activation
Indoles
Manifolds
N-alkylindoles
organic chemistry
Zirconium
zirconium catalyst
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Summary:Highly position selective alkylations of N‐alkylindoles at C7‐positions have been enabled by cationic zirconium complexes. The strategy provides a straightforward access to install alkyl groups at C7‐positions of indoles without a complex directing group. Mechanistic studies provided support for the importance of Brønsted acids in the catalytic manifold. A highly regioselective alkylation of N‐alkylindole at C7‐positions mediated by cationic zirconium complexes has been developed. This method provides a straightforward strategy to install alkyl groups at C7‐positions of indoles, without introducing complex directing groups. Mechanistic studies revealed the key importance of acids within the catalytic manifold (see scheme).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201901268