Issue 47, 2018
From the journal:

Chemical Communications

Nucleophilic addition of tertiary propargylic amines to arynes followed by a [2,3]-sigmatropic rearrangement†

Meng-Guang Zhou,a   Rui-Han Daia  and  Shi-Kai Tian ORCID logo *a  

* Corresponding authors

a Hefei National Laboratory for Physical Sciences at the Microscale, Center for Excellence in Molecular Synthesis, and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China
E-mail: tiansk@ustc.edu.cn

Abstract

In the presence of 2-(trimethylsilyl)aryl triflates as aryne precursors under mild conditions, a range of tertiary propargylic amines bearing electron-withdrawing groups were converted to quaternary propargylic ammonium ylides followed by a [2,3]-sigmatropic rearrangement to afford structurally diverse amino-substituted allenes or conjugated dienes, depending on their structure, in moderate to good yields.

Graphical abstract: Nucleophilic addition of tertiary propargylic amines to arynes followed by a [2,3]-sigmatropic rearrangement

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C8CC02176G
Article type
Communication
Submitted
19 Mar 2018
Accepted
14 May 2018
First published
19 May 2018

Chem. Commun., 2018,54, 6036-6039

Permissions

Request permissions

Nucleophilic addition of tertiary propargylic amines to arynes followed by a [2,3]-sigmatropic rearrangement

M. Zhou, R. Dai and S. Tian, Chem. Commun., 2018, 54, 6036 DOI: 10.1039/C8CC02176G

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements