Fast microwave promoted palladium-catalyzed synthesis of phthalides from bromobenzyl alcohols utilizing DMF and MO(CO)(6) as carbon monoxide sources

A fast method utilizing in situ generated CO for the synthesis of phthalides has been developed. DMF and MO(CO)(6) were applied as two alternative CO-sources in these microwave promoted carbonylation-lactone formation reactions. MO(CO)(6) was found to be the more generally applicable CO-source and p...

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Bibliographic Details
Published inTetrahedron letters Vol. 45; no. 24; pp. 4635 - 4638
Main Authors Wu, XY, Mahalingam, AK, Wan, YQ, Alterman, M
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 07.06.2004
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
AMINOCARBONYLATIONS
INCREASING RATES
ASSISTED ORGANIC-CHEMISTRY
MO(CO)
DRUG DISCOVERY
phthalides
carbon monoxide source
CARBONYLATION
HETEROCYCLES
LACTONES
PHTHALIDEISOQUINOLINE
ARYL HALIDES
ANHYDRIDES
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Summary:A fast method utilizing in situ generated CO for the synthesis of phthalides has been developed. DMF and MO(CO)(6) were applied as two alternative CO-sources in these microwave promoted carbonylation-lactone formation reactions. MO(CO)(6) was found to be the more generally applicable CO-source and provided phthalides as well as dihydroisocoumarin, dihydroisoindone, and phthalimide from the corresponding aryl bromide via an efficient CO insertion within a 1 h reaction time. (C) 2004 Elsevier Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2004.04.110