Issue 40, 2019

Saturated oxygen and nitrogen heterocycles via oxidative coupling of alkyltrifluoroborates with alkenols, alkenoic acids and protected alkenylamines

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.

Graphical abstract: Saturated oxygen and nitrogen heterocycles via oxidative coupling of alkyltrifluoroborates with alkenols, alkenoic acids and protected alkenylamines

Supplementary files

Article information

Article type
Edge Article
Submitted
11 juin 2019
Accepted
17 août 2019
First published
19 août 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2019,10, 9265-9269

Saturated oxygen and nitrogen heterocycles via oxidative coupling of alkyltrifluoroborates with alkenols, alkenoic acids and protected alkenylamines

J. M. Shikora, C. Um, Z. M. Khoder and S. R. Chemler, Chem. Sci., 2019, 10, 9265 DOI: 10.1039/C9SC02835H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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