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α ‐Silyl Ethers as Hydroxymethyl Anion Equivalents in Photoinduced Radical Electron Transfer Additions
Author(s) -
Gutenberger Guido,
Steckhan Eberhard,
Blechert Siegfried
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19980316)37:5<660::aid-anie660>3.0.co;2-8
Subject(s) - chemistry , hydroxymethyl , radical , silylation , protonation , adduct , medicinal chemistry , carbanion , electron transfer , photochemistry , biphenyl , nucleophile , ion , stereochemistry , organic chemistry , catalysis
Abstract Nucleophilic α ‐hydroxymethyl radicals can be generated from α ‐silyl ethers by irradiation in the presence of 9,10‐anthracenedicarbonitrile (ADC) and biphenyl (BP). Under these conditions the hydroxymethyl radicals are not oxidized further but add directly to electron‐poor alkenes [Eq. (a); EWG=electron‐withdrawing group]. The radical adduct undergoes back electron transfer to form the carbanion, which is protonated. R=PhCH 2 , t BuMe 2 Si, Me; TMS=Me 3 Si.