Issue 100, 2018

Palladium-catalyzed intramolecular transfer hydrogenation & cycloaddition of p-quinamine-tethered alkylidenecyclopropanes to synthesize perhydroindole scaffolds

Abstract

A palladium(0)-catalyzed intramolecular transfer hydrogenation and cycloaddition of p-quinamine-tethered alkylidenecyclopropanes (ACPs) to synthesize perhydroindole scaffolds has been reported in this communication. Mechanistic investigations on the basis of deuterium labeling experiments suggest that the reaction proceeded through an oxidative addition of Pd(0) into the distal bond of the ACP moiety to afford a trimethylenemethane (TMM)–Pd intermediate followed by transfer hydrogenation using alcohol.

Graphical abstract: Palladium-catalyzed intramolecular transfer hydrogenation & cycloaddition of p-quinamine-tethered alkylidenecyclopropanes to synthesize perhydroindole scaffolds

Supplementary files

Article information

Article type
Communication
Submitted
14 Nov 2018
Accepted
19 Nov 2018
First published
20 Nov 2018

Chem. Commun., 2018,54, 14085-14088

Palladium-catalyzed intramolecular transfer hydrogenation & cycloaddition of p-quinamine-tethered alkylidenecyclopropanes to synthesize perhydroindole scaffolds

B. Cao, Y. Wei and M. Shi, Chem. Commun., 2018, 54, 14085 DOI: 10.1039/C8CC09041F

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