Copper-catalysed cyanoalkylative cycloetherification of alkenes to 1,3-dihydroisobenzofurans: development and application to the synthesis of citalopram

A copper-catalysed cyanoalkylative cycloetherification of alkenes was developed. Heating a solution of substituted (2-vinylphenyl) methanol in MeCN/MeOH (v/v 7/3) in the presence of a catalytic amount of copper(II) tetrafluoroborate hydrate [ Cu(BF4)(2)center dot 6H(2)O], bathophenanthroline, K3PO4,...

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Published inChemical communications (Cambridge, England) Vol. 52; no. 74; pp. 11100 - 11103
Main Authors Ha, Tu M., Wang, Qian, Zhu, Jieping
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 25.09.2016
Subjects
Alkenes
Catalysis
Catalysts
Chemistry
Chemistry, Multidisciplinary
Formations
Heating
Hydrates
Physical Sciences
Science & Technology
Synthesis
Transformations
ACTIVATED ALKENES
HETEROCYCLES
ALLYLIC ALCOHOLS
NOREPINEPHRINE TRANSPORTER
CARBOETHERIFICATION
BOND FUNCTIONALIZATION
ALKYL NITRILES
ACETONITRILE
CYANOMETHYLATION
UNACTIVATED ALKENES
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Summary:A copper-catalysed cyanoalkylative cycloetherification of alkenes was developed. Heating a solution of substituted (2-vinylphenyl) methanol in MeCN/MeOH (v/v 7/3) in the presence of a catalytic amount of copper(II) tetrafluoroborate hydrate [ Cu(BF4)(2)center dot 6H(2)O], bathophenanthroline, K3PO4, BnOH and (tBuO)(2) afforded 1,3-dihydroisobenzofurans (phthalanes) via formation of one C(sp(3))-C(sp(3)) and one C(sp(3))-O bonds. A concise synthesis of citalopram, a marketed anti-depressant drug, was accomplished by applying this novel synthetic transformation.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1359-7345
1364-548X
DOI:10.1039/c6cc06356j