- Synthesis of substituted benzenes and phenols by ring-closing olefin metathesis
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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 1,5,7trien-4-ones 9, which were prepared by oxidation of 7, furnished various substituted phenols 6 by automatic tautomerization.
- Yoshida, Kazuhiro,Takahashi, Hidetoshi,Imamoto, Tsuneo
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experimental part
p. 8246 - 8261
(2009/09/29)
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- Indenes via Fulvene Intermediates
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Substituted indenes are prepared from 1,4-dicarbonyl compounds by treatment with base and cyclopentadiene.
- Coe, Jotham W.,Vetelino, Michael G.,Kemp, Daniel S.
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p. 6627 - 6630
(2007/10/02)
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