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Journal articles
Deproto-metallation of N-arylated pyrroles and indoles using a mixed lithium–zinc base and regioselectivity-computed CH acidity relationship
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 ZnCl2·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.
Cited literature [32 references]
https://hal-univ-rennes1.archives-ouvertes.fr/hal-01248096
Contributor : Florence Mongin <>
Submitted on : Wednesday, December 23, 2015 - 5:32:12 PM
Last modification on : Tuesday, January 12, 2021 - 4:50:19 PM
Contributor : Florence Mongin <>
Submitted on : Wednesday, December 23, 2015 - 5:32:12 PM
Last modification on : Tuesday, January 12, 2021 - 4:50:19 PM
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bjoc 1860-5397-11-160.pdf
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