Rhodium-catalyzed rapid synthesis of substituted phenols from cyclobutenones and alkynes or alkenes via C–C bond cleavage

A novel rhodium-catalyzed synthesis of substituted phenols by the ring-opening reaction of cyclobutenones with alkynes as well as electron-deficient alkenes has been developed. Both reactions involve C–C bond cleavage of cyclobutenones, and an ( η 4-vinylketene)rhodium complex rather than a rhodacyc...

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Bibliographic Details
Published inTetrahedron letters Vol. 48; no. 16; pp. 2837 - 2839
Main Authors Kondo, Teruyuki, Niimi, Masatsugu, Nomura, Masato, Wada, Kenji, Mitsudo, Take-aki
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 16.04.2007
Elsevier
Subjects
Catalyst
Chemistry
Chemistry, Organic
Cyclobutenone
C–C Bond cleavage
Phenol
Physical Sciences
Rhodium
Science & Technology
Cyclobutenone
Phenol
Rhodium
C–C Bond cleavage
Catalyst
VINYLKETENE
cyclobutenone
INSERTION
catalyst
COMPLEXES
phenol
C-C bond cleavage
rhodium
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Summary:A novel rhodium-catalyzed synthesis of substituted phenols by the ring-opening reaction of cyclobutenones with alkynes as well as electron-deficient alkenes has been developed. Both reactions involve C–C bond cleavage of cyclobutenones, and an ( η 4-vinylketene)rhodium complex rather than a rhodacyclopentenone is considered to be a key intermediate.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2007.02.091