Issue 1, 2013

Photochemically induced radical alkynylation of C(sp3)–H bonds

Abstract

A general strategy for photochemical alkynylation of unreactive C(sp3)–H bonds has been developed. After C–H abstraction by the photo-excited benzophenone, a two-carbon unit was efficiently transferred to the generated radical from 1-tosyl-2-(trimethylsilyl)acetylene to afford the alkynylated product. The present reaction enables construction of various tri- and tetra-substituted carbons from heteroatom-substituted methylenes, methines and alkanes in a highly chemoselective fashion, and would serve as a new synthetic strategy for rapid construction of complex structures.

Graphical abstract: Photochemically induced radical alkynylation of C(sp3)–H bonds

Supplementary files

Article information

Article type
Paper
Submitted
11 Sep 2012
Accepted
12 Oct 2012
First published
16 Oct 2012

Org. Biomol. Chem., 2013,11, 164-169

Photochemically induced radical alkynylation of C(sp3)–H bonds

T. Hoshikawa, S. Kamijo and M. Inoue, Org. Biomol. Chem., 2013, 11, 164 DOI: 10.1039/C2OB26785C

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