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Pure Appl. Chem., 2003, Vol. 75, No. 8, pp. 1049-1054

Regio- and stereoselective functionalization of electron-deficient alkenes by organosilicon compounds via photoinduced electron transfer

K. Mizuno, T. Hayamizu and Hajime 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.