Engaging 1,7-diynes in a photocatalytic Kharasch-type addition/1,5-(SN′′)-substitution cascade toward β-gem-dihalovinyl carbonyls

Dan Wu; Wen-Juan Hao; Qian Rao; Yi Lu; Shu-Jiang Tu; Bo Jiang

doi:10.1039/D0CC07880H

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

Engaging 1,7-diynes in a photocatalytic Kharasch-type addition/1,5-(S_N′′)-substitution cascade toward β-gem-dihalovinyl carbonyls†

Dan Wu,^a Wen-Juan Hao,

*^a Qian Rao,^a Yi Lu,^a Shu-Jiang Tu

*^a and Bo Jiang

*^a

Author affiliations

* Corresponding authors

^a School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou, P. R. China
E-mail: wjhao@jsnu.edu.cn, laotu@jsnu.edu.cn, jiangchem@jsnu.edu.cn

Abstract

A new and general photocatalytic Kharasch-type addition/1,5-(S_N′′)-substitution cascade of 1,7-diynes with alkyl halides such as BrCCl₃ and CBr₄ was reported for the first time, and used to produce 65 hitherto unreported β-gem-dihalovinyl ketones/aldehydes with moderate to excellent yields in a highly regioselective manner. This reaction tolerates a wide scope of substrates, which offers a green and efficient entry to fabricate synthetically important β-gem-dihalovinyl carbonyl scaffolds. Notably, the late-stage application of these resulting β-gem-dihalovinyl carbonyls shows high and unique reactivity profiles and demonstrates the versatility of their derivatization.

Download options Please wait...

Supplementary files

Article information

DOI: https://doi.org/10.1039/D0CC07880H
Article type: Communication
Submitted: 03 Dec 2020
Accepted: 14 Jan 2021
First published: 14 Jan 2021

Download Citation

Chem. Commun., 2021,57, 1911-1914

Permissions

Request permissions

Engaging 1,7-diynes in a photocatalytic Kharasch-type addition/1,5-(S_N′′)-substitution cascade toward β-gem-dihalovinyl carbonyls

D. Wu, W. Hao, Q. Rao, Y. Lu, S. Tu and B. Jiang, Chem. Commun., 2021, 57, 1911 DOI: 10.1039/D0CC07880H

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.

Social activity

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

Chemical Communications