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Issue 31, 2014
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Breaking the dichotomy of reactivity vs. chemoselectivity in catalytic SN1 reactions of alcohols

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Abstract

The inability to decouple Lewis acid catalysis from undesirable Brønsted acid catalysed side reactions when water or other protic functional groups are necessarily present has forced chemists to choose between powerful but harsh catalysts or poor but mild ones, a dichotomy that restricts the substrate scope of dehydrative transformations such as the direct SN1 reaction of alcohols. A systematic survey of Lewis and Brønsted acids reveals that the strong non-hydrolyzable Lewis acid B(C6F5)3 leads to highly chemoselective alcohol substitution in the presence of acid-sensitive alkenes, protecting groups and other functional groups without the typical compromise in reaction rates, substrate scope and catalyst loading.

Graphical abstract: Breaking the dichotomy of reactivity vs. chemoselectivity in catalytic SN1 reactions of alcohols

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Supplementary files

Article information


Submitted
09 Jan 2014
Accepted
23 Jun 2014
First published
24 Jun 2014

Org. Biomol. Chem., 2014,12, 5990-5994
Article type
Paper
Author version available

Breaking the dichotomy of reactivity vs. chemoselectivity in catalytic SN1 reactions of alcohols

M. Hellal, F. C. Falk, E. Wolf, M. Dryzhakov and J. Moran, Org. Biomol. Chem., 2014, 12, 5990
DOI: 10.1039/C4OB01265H

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