Tetrahedron p. 4031 - 4038 (1990)
Update date:2022-08-05
Topics: Alkylation Regioselectivity Yield Catalyst Steric hindrance Mass spectrometry (MS) Nucleophilic substitution Nuclear Magnetic Resonance (NMR) Oxidative Addition Grignard Reagent Radical mechanism Heteroaryl Silyl group Gas chromatography (GC) Inert atmosphere Reaction quenching Organolithium compound
Epifani, Erbana
Florio, Saverio
Troisi, Luigino
Heteroaryl alkyl metals 3 undergo methylation and ethylation upon treatment with bistrimethylsilylperoxide 1a and bistriethylsilylperoxide 1b.Benzothiazolylderivatives 3c-d and 3h-j react with 1a giving trimethylsilyloxylation other than methylation products.The reaction of 3a-b with 1a leads also to the trimethylsilylation product 5.The reaction of 3g, 3c and 3k with 1b provides the ethylated derivatives 2h, 2d and 2n respectively.No reaction occurred when 3c was treated with 1c.
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Doi:10.1021/jo00830a006
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