Issue 17, 2018
From the journal:

Chemical Communications

Chiral triazolylidene-Pd-PEPPSI: synthesis, characterization, and application in asymmetric Suzuki–Miyaura cross-coupling†

Ryosuke Haraguchi, ORCID logo *a   Shun Hoshino,a   Tatsuro Yamazakia  and  Shin-ichi Fukuzawa*a  

* Corresponding authors

a Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan
E-mail: ryo1229@kc.chuo-u.ac.jp, orgsynth@kc.chuo-u.ac.jp

Abstract

A chiral triazolylidene-Pd-PEPPSI (PEPPSI = pyridine, enhanced, precatalyst, preparation, stabilization, initiation) complex with ferrocene-based planar chirality has been synthesized and characterized. Investigation of the electronic and steric nature of this complex revealed its powerful electron-donating ability (TEP 2044 cm−1) and high steric bulk (%Vbur = 42.2). These unique properties allow the complex to exhibit very high catalytic activity (TON = 420) for asymmetric Suzuki–Miyaura cross-coupling, providing the coupling product with good enantioselectivity (75% ee).

Graphical abstract: Chiral triazolylidene-Pd-PEPPSI: synthesis, characterization, and application in asymmetric Suzuki–Miyaura cross-coupling

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Article information

DOI
https://doi.org/10.1039/C7CC09960F
Article type
Communication
Submitted
31 Dec 2017
Accepted
29 Jan 2018
First published
30 Jan 2018

Chem. Commun., 2018,54, 2110-2113

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Chiral triazolylidene-Pd-PEPPSI: synthesis, characterization, and application in asymmetric Suzuki–Miyaura cross-coupling

R. Haraguchi, S. Hoshino, T. Yamazaki and S. Fukuzawa, Chem. Commun., 2018, 54, 2110 DOI: 10.1039/C7CC09960F

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