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A Metathesis Approach to Aromatic Heterocycles
Author(s) -
Donohoe Timothy J.,
Orr Allan J.,
Gosby Katherine,
Bingham Matilda
Publication year - 2005
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.200500113
Subject(s) - chemistry , allene , metathesis , ring closing metathesis , salt metathesis reaction , allylic rearrangement , combinatorial chemistry , methanol , coupling reaction , ring (chemistry) , organic chemistry , catalysis , polymerization , polymer
Abstract The ring closing metathesis (RCM) reaction can be used to prepare substituted furans and pyrroles. By utilising a Pd‐catalysed coupling reaction with methoxyallene, allylic alcohols and sulfonamides can be converted into substrates that are ideal precursors to ring closing metathesis. After the RCM reaction is complete, the addition of acid promotes an elimination of methanol to form the fully aromatised system. A range of different substitution patterns and functional groups are compatible with this sequence. Double allene coupling, RCM and elimination reactions are also possible and allow the formation of biaryl systems. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)