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)26H2O], bathophenanthroline, K3PO4, BnOH and (tBuO)2 afforded 1,3-dihydroisobenzofurans (phthalanes) via formation of one C(sp3)–C(sp3) and one C(sp3)–O bonds. A concise synthesis of citalopram, a marketed anti-depressant drug, was accomplished by applying this novel synthetic transformation.
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Ha, T. M., Wang, Q., & Zhu, J. (2016). Copper-catalysed cyanoalkylative cycloetherification of alkenes to 1,3-dihydroisobenzofurans: development and application to the synthesis of citalopram. Chemical Communications (ChemComm), 52(74), 11100–11103. https://doi.org/10.1039/C6CC06356J
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WOS:000384202000014
2016
52
74
11100
11103
REVIEWED
EPFL