Issue 9, 2017

A photoinduced reaction of perfluoroalkyl halides with 1,3-diarylprop-2-yn-1-ones catalyzed by DABSO

Abstract

The sulfur dioxide surrogate of DABCO·(SO2)2 is used as an efficient catalyst for the cleavage of the perfluoroalkyl-halogen bond under visible-light irradiation for the first time. This unexpected reaction of perfluoroalkyl halides and 1,3-diarylprop-2-yn-1-ones catalyzed by DABCO·(SO2)2 in the presence of visible light proceeds smoothly, leading to 3-fluorinated indenones in good yields. During the reaction process, the cleavage of the perfluoroalkyl-halogen bond and subsequent radical oxidative cyclization are involved under metal-free conditions. A broad reaction scope is observed. Moreover, a plausible mechanism supported by theoretical calculations is proposed.

Graphical abstract: A photoinduced reaction of perfluoroalkyl halides with 1,3-diarylprop-2-yn-1-ones catalyzed by DABSO

Supplementary files

Article information

Article type
Research Article
Submitted
10 Apr 2017
Accepted
29 May 2017
First published
31 May 2017

Org. Chem. Front., 2017,4, 1745-1750

A photoinduced reaction of perfluoroalkyl halides with 1,3-diarylprop-2-yn-1-ones catalyzed by DABSO

Y. Li, Y. Lu, R. Mao, Z. Li and J. Wu, Org. Chem. Front., 2017, 4, 1745 DOI: 10.1039/C7QO00279C

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