Issue 33, 2015

Asymmetric Suzuki–Miyaura cross-coupling of 1-bromo-2-naphthoates using the helically chiral polymer ligand PQXphos

Abstract

A single-handed helical polymer ligand PQXphos afforded axially chiral biaryl esters with high enantioselectivities in asymmetric Suzuki–Miyaura cross-coupling. The use of naphthyl bromide bearing a 2,4-dimethyl-3-pentyl ester resulted in both high yields and high enantioselectivities. Either enantiomer could be synthesized selectively by using a single PQXphos through a solvent-dependent switch of the helical chirality.

Graphical abstract: Asymmetric Suzuki–Miyaura cross-coupling of 1-bromo-2-naphthoates using the helically chiral polymer ligand PQXphos

Supplementary files

Article information

Article type
Communication
Submitted
05 Feb 2015
Accepted
20 Mar 2015
First published
20 Mar 2015

Chem. Commun., 2015,51, 7211-7214

Asymmetric Suzuki–Miyaura cross-coupling of 1-bromo-2-naphthoates using the helically chiral polymer ligand PQXphos

Y. Akai, L. Konnert, T. Yamamoto and M. Suginome, Chem. Commun., 2015, 51, 7211 DOI: 10.1039/C5CC01074H

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