Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 17, Issue 15, Pages 4064-4075Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201002248
Keywords
alkylation; electrophilic aromatic substitution; heterocycles; pyrroles; regioselectivity
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Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan [21750107]
- Nissan Chemical Industries, L.T.D.
- Grants-in-Aid for Scientific Research [21750107] Funding Source: KAKEN
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beta-Alkylpyrroles are key structural motifs found in many natural products and biologically active compounds as well as functional organic materials. For this reason, synthetic chemists continue to be interested in construction of the framework of beta-alkylpyrroles. Due to sufficient aromaticity and pi-excessive nature of pyrroles, a straightforward approach to beta-alkylpyrroles should be electrophilic aromatic substitution (SEAr) toward the pyrrole ring. However, since a primary nucleophilic site of pyrroles is an alpha-position, some trick is required to direct incoming alkyl electrophiles toward a beta-position. This Concept article focuses on presenting previous efforts that have been devoted to the synthesis of beta-alkylpyrroles, mainly through the SEAr route.
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