Issue 95, 2014
From the journal:

Chemical Communications

An efficient generation method and remarkable reactivities of 3-triflyloxybenzyne†

Suguru Yoshida,a   Keisuke Uchida,a   Kazunobu Igawa,b   Katsuhiko Tomookab  and  Takamitsu Hosoya*a  

* Corresponding authors

a Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan
E-mail: thosoya.cb@tmd.ac.jp

b Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasuga-koen, Kasuga, Fukuoka 816-8580, Japan

Abstract

3-Triflyloxybenzyne was generated via an iodine–magnesium exchange reaction of 1,3-bis(triflyloxy)-2-iodobenzene using the trimethylsilylmethyl Grignard reagent. Various arynophiles and nucleophiles reacted regioselectively with 3-triflyoxybenzyne to afford cycloadducts and unique aryl triflones, which were provided via thia-Fries rearrangement.

Graphical abstract: An efficient generation method and remarkable reactivities of 3-triflyloxybenzyne

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C4CC07058E
Article type
Communication
Submitted
07 Sep 2014
Accepted
30 Sep 2014
First published
08 Oct 2014

Chem. Commun., 2014,50, 15059-15062

Permissions

Request permissions

An efficient generation method and remarkable reactivities of 3-triflyloxybenzyne

S. Yoshida, K. Uchida, K. Igawa, K. Tomooka and T. Hosoya, Chem. Commun., 2014, 50, 15059 DOI: 10.1039/C4CC07058E

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