Stereocontrolled C(sp3)–P bond formation with non-activated alkyl halides and tosylates

Chu-Ting Yang; Jun Han; Jun Liu; Yi Li; Fan Zhang; Mei Gu; Sheng Hu; Xiaolin Wang

doi:10.1039/C7RA02766D

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

Stereocontrolled C(sp³)–P bond formation with non-activated alkyl halides and tosylates†

Chu-Ting Yang,

*^a Jun Han,^a Jun Liu,^a Yi Li,^a Fan Zhang,^a Mei Gu,^a Sheng Hu^a and Xiaolin Wang*^a

Author affiliations

* Corresponding authors

^a Institute of Nuclear Physics and Chemistry, China Academy of Engineering Physics, Mianyang, Sichuan, P. R. China
E-mail: xlwang@caep.cn, yangchuting@caep.cn

Abstract

The C(sp³)–P bond is formed via the reaction between P–H compounds and non-activated alkyl electrophiles, especially secondary alkyl halides and tosylates. This reaction proceeds via an S_N2 mechanism with inversion of configuration, so it can be used to form C–P bonds with stereocontrol from chiral secondary alcohols.

Download options Please wait...

Supplementary files

Article information

DOI: https://doi.org/10.1039/C7RA02766D
Article type: Paper
Submitted: 07 Mar 2017
Accepted: 28 Apr 2017
First published: 08 May 2017
This article is Open Access

Download Citation

RSC Adv., 2017,7, 24652-24656

Permissions

Request permissions

Stereocontrolled C(sp³)–P bond formation with non-activated alkyl halides and tosylates

C. Yang, J. Han, J. Liu, Y. Li, F. Zhang, M. Gu, S. Hu and X. Wang, RSC Adv., 2017, 7, 24652 DOI: 10.1039/C7RA02766D

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Social activity

Fetching data from CrossRef.
This may take some time to load.

RSC Advances