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17 Dec 17:34

A Chiral Nitrogen Ligand for Enantioselective, Iridium-Catalyzed Silylation of Aromatic C−H Bonds

by Bo Su, Tai-Gang Zhou, Xian-Wei Li, Xiao-Ru Shao, Pei-Lin Xu, Wen-Lian Wu, John F. Hartwig, Zhang-Jie Shi

Abstract

Iridium catalysts containing dative nitrogen ligands are highly active for the borylation and silylation of C−H bonds, but chiral analogs of these catalysts for enantioselective silylation reactions have not been developed. We report a new chiral pyridinyloxazoline ligand for enantioselective, intramolecular silylation of symmetrical diarylmethoxy diethylsilanes. Regioselective and enantioselective silylation of unsymmetrical substrates was also achieved in the presence of this newly developed system. Preliminary mechanistic studies imply that C−H bond cleavage is irreversible, but not the rate-determining step.

Thumbnail image of graphical abstract

Iridium works now: A new chiral pyridinyloxazoline ligand was developed, which enables enantioselective, intramolecular silylation of symmetrical diarylmethoxy diethylsilanes. Regioselective and enantioselective silylation of unsymmetrical substrates was also achieved in the presence of this newly developed system.

23 Feb 17:19

Asymmetric [3 + 2] cycloaddition of donor-acceptor aziridines with aldehydes via carbon-carbon bond cleavage

Chem. Sci., 2016, 7,3775-3779
DOI: 10.1039/C5SC04151A, Edge Article
Open Access Open Access
Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Yuting Liao, Xiaohua Liu, Yu Zhang, Yali Xu, Yong Xia, Lili Lin, Xiaoming Feng
An enantioselective [3 + 2] annulation of donor-acceptor aziridines with aldehydes utilizing a relay catalyst system of Nd(OTf)3/N,N[prime or minute]-dioxide/LiNTf2 has been realized.
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30 Jul 16:15

(E)-Trimethyl(perfluoroprop-1-enyl)silane As a Reagent to Transfer Perfluoroprop-1-enyl Group to Ketones and Aldehydes Catalyzed by Fluoride

by Roman B. Larichev, Viacheslav A. Petrov, Gerard J. Grier, Mario J. Nappa, William J. Marshall, Alexander A. Marchione and Rebecca J. Dooley

TOC Graphic

Organic Process Research & Development
DOI: 10.1021/op5001385
20 Apr 15:21

Copper(I)-Catalyzed Nucleophilic Addition of Ynamides to Acyl Chlorides and Activated N-Heterocycles

by Peng Zhang, Andrea M. Cook, Yang Liu and Christian Wolf

TOC Graphic

The Journal of Organic Chemistry
DOI: 10.1021/jo500365h