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 3 2018
Accepted
25 5 2018
First published
26 5 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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