Saturated oxygen and nitrogen heterocycles via oxidative coupling of alkyltrifluoroborates with alkenols, alkenoic acids and protected alkenylamines. Issue 40 (23rd August 2019)

• Record Type: Journal Article
• Authors: Shikora, Jonathan M.; Um, Chanchamnan; Khoder, Zainab M.; Chemler, Sherry R.
• Is Part Of: Chemical science. Volume 10:Issue 40(2019)
• Page Start: 9265
• Page End: 9269
• Publication Date: 2019-08-23
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c9sc02835h
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : The oxidative coupling of alkyltrifluoroborates with heteroatom-tethered vinylarenes leads to a broad range of saturated oxygen and nitrogen heterocycles. Abstract : Saturated heterocycles are important components of many bioactive compounds. The method disclosed herein enables a general route to a range of 5-, 6- and 7-membered oxygen and nitrogen heterocycles by coupling potassium alkyltrifluoroborates with heteroatom-tethered alkenes, predominantly styrenes, under copper-catalyzed conditions, in the presence of MnO2 . The method was applied to the synthesis of the core of the anti-depressant drug citalopram. The reaction scope and observed reactivity is consistent with a polar/radical mechanism involving intermolecular addition of the alkyl radical to the alkene followed by [Cu(iii )]-facilitated C–O (or C–N) bond forming reductive elimination.