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Issue 8, 2019
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Pd-catalyzed γ-arylation of γ,δ-unsaturated O-carbamates via an unusual haptotropic rearrangement

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Abstract

An unusual γ-selectivity was observed in the arylation of γ,δ-unsaturated O-carbamates involving directed lithiation, transmetallation to zinc and Negishi coupling, when a specific combination of aryl electrophile and phosphine ligand is employed. Mechanistic studies indicate that an unusual, stereospecific haptotropic rearrangement of the palladium–diene intermediate is involved.

Graphical abstract: Pd-catalyzed γ-arylation of γ,δ-unsaturated O-carbamates via an unusual haptotropic rearrangement

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Article information


Submitted
13 Nov 2018
Accepted
21 Dec 2018
First published
26 Dec 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 2331-2335
Article type
Edge Article

Pd-catalyzed γ-arylation of γ,δ-unsaturated O-carbamates via an unusual haptotropic rearrangement

T. Royal and O. Baudoin, Chem. Sci., 2019, 10, 2331
DOI: 10.1039/C8SC05058A

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