In:
Beilstein Journal of Organic Chemistry, Beilstein Institut, Vol. 11 ( 2015-08-24), p. 1475-1485
Abstract:
The synthesis of N-arylated pyrroles and indoles is documented, as well as their functionalization by deprotonative metallation using the base in situ prepared from LiTMP and ZnCl 2 ·TMEDA (1/3 equiv). With N -phenylpyrrole and - indole, the reactions were carried out in hexane containing TMEDA which regioselectively afforded the 2-iodo derivatives after subsequent iodolysis. With pyrroles and indoles bearing N-substituents such as 2-thienyl, 3-pyridyl, 4-methoxyphenyl and 4-bromophenyl, the reactions all took place on the substituent, at the position either adjacent to the heteroatom (S, N) or ortho to the heteroatom-containing substituent (OMe, Br). The CH acidities of the substrates were determined in THF solution using the DFT B3LYP method in order to rationalize the experimental results.
Type of Medium:
Online Resource
ISSN:
1860-5397
Language:
English
Publisher:
Beilstein Institut
Publication Date:
2015
detail.hit.zdb_id:
2192461-2
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