Issue 11, 2011
From the journal:

Chemical Science

Opening the silole ring: Efficient and specific cleavage of the endo-C(sp2)-Si bond with AcOH/ROH system†

Qian Luo,a   Chao Wang,bc   Yuexing Li,a   Kunbing Ouyang,a   Li Gu,a   Masanobu Uchiyamabc  and  Zhenfeng Xi*ad  

* Corresponding authors

a Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing, China
E-mail: zfxi@pku.edu.cn
Fax: +86-10-62751708
Tel: +86-10-62759728

b Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, Japan

c Advanced Science Institute (ASI), RIKEN, 2-1 Hirosawa, Wako, Saitama, Japan

d State Key Laboratory of Organometallic Chemistry, SIOC, CAS, Shanghai, China

Abstract

An efficient and specific cleavage of the endo-C(sp2)-Si bond of silole rings was developed. The stable silole ring was effectively opened in an unexpected regioselectivity by using an AcOH/ROH system, in which the AcOH behaved as a catalyst and the ROH as a nucleophile. Depending on the nature of the substituents at the 2- and 5-positions of the silole ring, the cooperative effect of the AcOH/ROH system exclusively cleaved one of the two endo-C-Si bonds to afford silylbutadiene derivatives.

Graphical abstract: Opening the silole ring: Efficient and specific cleavage of the endo-C(sp2)-Si bond with AcOH/ROH system

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C1SC00356A
Article type
Edge Article
Submitted
11 Jun 2011
Accepted
08 Aug 2011
First published
26 Aug 2011

Chem. Sci., 2011,2, 2271-2274

Permissions

Request permissions

Opening the silole ring: Efficient and specific cleavage of the endo-C(sp2)-Si bond with AcOH/ROH system

Q. Luo, C. Wang, Y. Li, K. Ouyang, L. Gu, M. Uchiyama and Z. Xi, Chem. Sci., 2011, 2, 2271 DOI: 10.1039/C1SC00356A

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