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Synthesis of Substituted Benzenes and Phenols by Ring‐Closing Olefin Metathesis
Author(s) -
Yoshida Kazuhiro,
Takahashi Hidetoshi,
Imamoto Tsuneo
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200800484
Subject(s) - olefin metathesis , ring closing metathesis , closing (real estate) , phenols , olefin fiber , ring (chemistry) , metathesis , acyclic diene metathesis , chemistry , ring opening metathesis polymerisation , organic chemistry , catalysis , political science , law , polymerization , polymer
New synthetic approaches to substituted aromatic compounds are reported. Ring‐closing olefin metathesis (RCM)/dehydration and RCM/tautomerization are the key processes in the synthesis of substituted benzenes 3 and phenols 6 , respectively. Readily accessible 1,5,7‐trien‐4‐ols 7 , which are the precursors of benzenes, were prepared from β‐halo‐α,β‐unsaturated aldehydes 11 or β‐halo‐α,β‐unsaturated esters 19 by utilizing reliable transformations in which cross‐coupling with vinylic metal reagents 12 and allylation with allylic metal reagents 13 were employed as carbon–carbon bond forming reactions. RCM of 7 , followed by dehydration, afforded a wide variety of substituted benzenes 3 . In addition, RCM of 1,5,7‐trien‐4‐ones 9 , which were prepared by oxidation of 7 , furnished various substituted phenols 6 by automatic tautomerization.