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Iron‐Catalyzed C–H Bond Functionalization for the Exclusive Synthesis of Pyrido[1,2‐ a ]indoles or Triarylmethanols
Author(s) -
Karthikeyan Iyyanar,
Sekar Govindasamy
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403233
Subject(s) - chemistry , amination , intramolecular force , catalysis , nucleophile , pyridine , ring (chemistry) , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry
The efficient and selective iron‐catalyzed C–H activation of 2‐benzhydrylpyridine derivatives was employed for the preparation of pyrido[1,2‐ a ]indoles through an intramolecular C–H amination reaction. In the presence of molecular oxygen as the sole oxidant, the same 2‐benzhydrylpyridines were also used for the synthesis of the corresponding tertiary alcohols. In these approaches, the iron catalyst was used to selectively activate the C(sp 2 )–H bond of 2‐benzhydrylpyridine, in the case of the intramolecular ring‐closing C–H amination reaction in which the pyridine nitrogen atom was a directing group as well as a nucleophile, and the C(sp 3 )–H bond of the same compound, in the case of the oxidation reaction to give the corresponding triaryl carbinol.