Issue 50, 2018

Divergent synthesis of CF3-substituted polycyclic skeletons based on control of activation site of acid catalysts

Abstract

We report a divergent synthesis of CF3-substituted fused skeletons based on precise control of the activation site through the selection of acid catalysts. When trifluoromethyl ketones with an ortho-phenethyl ether group were treated with a catalytic amount of Sc(OTf)3, a hydride shift triggered C(sp3)–H bond functionalization proceeded to give CF3-substituted isochromene derivatives by selective activation of the carbonyl group. In sharp contrast, CF3-substituted bicyclo[3.3.1]nonanes were obtained exclusively via the activation of ether oxygen initiated sequential reactions (nucleophilic attack of carbonyl oxygen, and intramolecular Friedel–Crafts reaction) under strong Brønsted acid catalysis (Tf2NH).

Graphical abstract: Divergent synthesis of CF3-substituted polycyclic skeletons based on control of activation site of acid catalysts

Supplementary files

Article information

Article type
Communication
Submitted
26 mar 2018
Accepted
25 mai 2018
First published
26 mai 2018

Chem. Commun., 2018,54, 6927-6930

Divergent synthesis of CF3-substituted polycyclic skeletons based on control of activation site of acid catalysts

K. Yokoo and K. Mori, Chem. Commun., 2018, 54, 6927 DOI: 10.1039/C8CC02377H

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