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Multifunctional 2‐ and 3‐Fluoropyrroles
Author(s) -
Heeran Darren,
Sandford Graham
Publication year - 2019
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.201900185
Subject(s) - chemistry , carbanion , regioselectivity , electrophile , combinatorial chemistry , electrophilic substitution , drug discovery , electrophilic addition , computational chemistry , organic chemistry , catalysis , biochemistry
Sequential reaction cascades for the synthesis of polysubstituted 2‐ and 3‐fluoropyrrole derivatives from common polybromopyrrole precursors have been developed. A strategic variation of a combination of regioselective debromolithiation followed by trapping of the corresponding carbanions by electrophilic fluorination and Pd catalysed cross‐coupling reactions allows access to polyfunctional fluoropyrrole products by methodology applicable to drug discovery programs, extending the range of five‐membered fluoroazaheteroaromatic derivatives potentially available for incorporation into screening libraries.