A New Dimension in Radical Chain Group Transfer Reaction by Photosensitized Electron Transfer (PET) Reductive Activation of PhSeSiR_3

摘要

Despite the drawbacks associated with tin hydrides, most of the recent applications of radical reactions in organic synthesis are based on the use of this reagent. While alternative approaches involving the silyl radical which is a better halophile than its tin radical counterpart, have partially overcome the limitations of the tin reagent, the high cost of its precursor tris(trimethylsilyl)silane (TMSS) and the loss of functionality during the last chain propagation step has limited its popularityamong organic chemists. To circumvent the known limitations of these two reagents, and the necessity for a better reagent for radical chain reactions in organic synthesis, we introduce here PhSeSiR_3 1 (R_3 = Ph_2tBu). which under PET (photosensitized electron transfer) reductive reaction conditions initiates radical chain group transfer reactions (Scheme 1).