Journal
CHEMICAL COMMUNICATIONS
Volume 52, Issue 74, Pages 11100-11103Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6cc06356j
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Funding
- EPFL (Switzerland)
- Swiss National Science Foundation (SNSF)
- Swiss National Centres of Competence in Research (NCCR-Chemical biology)
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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.
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