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An Improved Ring‐Closing Metathesis Approach to Fluorinated and Trifluoromethylated Nitrogen Heterocycles
Author(s) -
De Matteis Valeria,
Dufay Olivier,
Waalboer Dennis C. J.,
van Delft Floris L.,
Tiebes Jörg,
Rutjes Floris P. J. T.
Publication year - 2007
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.200601119
Subject(s) - chemistry , ring closing metathesis , trifluoromethyl , metathesis , sulfonamide , pyrrole , combinatorial chemistry , mitsunobu reaction , salt metathesis reaction , ring (chemistry) , surface modification , organic chemistry , polymerization , polymer , alkyl
Abstract The synthesis of fluoro‐ and trifluoromethyl‐containing N ‐sulfonylated nitrogen heterocycles is described. A first crucial step is a Mitsunobu functionalization of intermediate sulfonamides using commercially available unsaturated alcohols, which gives efficient access to fluorinated ring‐closing metathesis (RCM) precursors. Key step is an RCM reaction of these precursors leading to the corresponding fluoro‐ and trifluoromethyl‐containing heterocyclic building blocks. Furthermore, aminopalladation of the same sulfonamide intermediates provides access to trifuoromethyl‐containing pyrrole derivatives.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)