Photochemical monoalkylation of propanedinitrile by electron-rich alkenes

Maki Ohashi; Keisuke Nakatani; Hajime Maeda; Kazuhiko Mizuno

doi:10.1021/ol800862x

Photochemical monoalkylation of propanedinitrile by electron-rich alkenes

Org Lett. 2008 Jul 3;10(13):2741-3. doi: 10.1021/ol800862x. Epub 2008 Jun 7.

Authors

Maki Ohashi¹, Keisuke Nakatani, Hajime Maeda, Kazuhiko Mizuno

Affiliation

¹ Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan.

PMID: 18537243
DOI: 10.1021/ol800862x

Abstract

The synthesis of monoalkylated propanedinitriles was achieved upon photoirradiation of MeCN/H(2)O solutions containing propanedinitrile (1; malononitrile) and electron-rich alkenes in the presence of lithium carbonate and a catalytic amount of 9-cyanophenanthrene or redox-type photosensitizers (electron-mediating photosensitizers), through regioselective anti-Markovnikov photochemical polar addition of 1 into electron-rich alkenes. With 2,5-dimethyl-2,4-hexadiene (2g) as an electron-rich alkene, propanedinitrile-incorporated dimer 4g was obtained.