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Base‐Mediated Direct Arylation of Pyrrole Derivatives
Author(s) -
Vakuliuk Olena,
Koszarna Beata,
Gryko Daniel T.
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000723
Subject(s) - chemistry , benzofuran , indolizine , lithium (medication) , aryl , catalysis , pyrrole , alkyl , base (topology) , medicinal chemistry , combinatorial chemistry , organic chemistry , medicine , mathematical analysis , mathematics , endocrinology
It appears that transition metal catalysts are not necessary to perform the direct arylation of electron‐rich heterocycles with aryl iodides and bromides. Lithium tert‐ butoxide in DMF promotes this reaction for a variety of N ‐alkyl‐ and N ‐arylpyrroles as well as for benzofuran and some other electron‐rich aromatic compounds and provides the desired products in moderate to high yields. In contrast to all previous reports on the Pd‐catalyzed direct arylation of indolizine, the reaction mediated by lithium tert‐ butoxide proceeds selectively at position 5.