Accessing highly functionalized cyclopentanoids via a cascade palladation approach: unprecedented benzylic C–H activation towards cyclopentenoindanes?

Chemical Communications Pub Date: 2018-02-23 DOI: 10.1039/C7CC09521J

Abstract

A Pd-catalyzed synthesis of 3,4,5-trisubstituted cyclopentenes from diazabicyclic olefins and o-iodobenzoates has been developed. The hitherto unknown cascade process involves three stages: carbopalladation, oxypalladation and a Tsuji–Trost reaction. We have also developed a facile route involving a novel benzylic C–H activation towards cyclopentenoindane moieties.

Graphical abstract: Accessing highly functionalized cyclopentanoids via a cascade palladation approach: unprecedented benzylic C–H activation towards cyclopentenoindanes
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