Issue 30, 2019

Palladium-catalyzed enantioselective alkenylation of alkenylbenzene derivatives

Abstract

A regioselective and enantioselective palladium-catalyzed relay Heck alkenylation of alkenylbenzene derivatives to construct remote stereocenters is disclosed. Various β-substituted styrenes were readily obtained in moderate yields with good to excellent levels of enantioselectivity. This strategy provides rapid access to enantioenriched δ, ε, ζ, and η-alkenyl aryl compounds from simple starting materials. Mechanistic studies suggest that termination of the relay reaction is controlled by affinity of the arene for the Pd complex during migration.

Graphical abstract: Palladium-catalyzed enantioselective alkenylation of alkenylbenzene derivatives

Supplementary files

Article information

Article type
Edge Article
Submitted
16 May 2019
Accepted
12 Jun 2019
First published
17 Jun 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2019,10, 7246-7250

Palladium-catalyzed enantioselective alkenylation of alkenylbenzene derivatives

Z. Chen, J. Liu, J. Guo, M. Loch, R. J. DeLuca and M. S. Sigman, Chem. Sci., 2019, 10, 7246 DOI: 10.1039/C9SC02380A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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