Regio- and stereoselective functionalization of electron-deficient alkenes by organosilicon compounds via photoinduced electron transfer
K. Mizuno, T. Hayamizu, and H. Maeda
Department of Applied Chemistry, Graduate School of
Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Sakai, Osaka
599-8531, Japan
Abstract: Regio- and stereoselective photoallylation
of electron-deficient alkenes by use of allylic silanes via photoinduced
electron transfer has been described. Similar photoinduced functionalization
reactions such as arylmethylation, alkylation, and silylation can be
achieved by using a variety of organosilicon compounds. These photoreactions
proceed via radical cations of organosilicon compounds and radical anions
of electron-deficient alkenes as reactive intermediates. The key step
of the photoreactions is the attack of carbon radicals, which are generated
from the radical cations of organosilicon compounds, on the radical
anions of alkenes. The mechanism of the regio- and stereoselective photofunctionalization
is discussed.
* Lectures presented at the XIXth IUPAC Symposium on Photochemistry, Budapest, Hungary, 14�19 July 2002. Other presentations are published in this issue, pp.999�1090.
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