Reaction of silyl dithiolanes with electrophiles can be efficiently promoted by catalytic amounts of tetrabutylammonium phenoxide (PhONn–Bu4), leading to a convenient access to functionalized dithiolanes. PhONn–Bu4 proved effective also in promoting reactions of silylated sulfides such as PhSTMS and HMDST as well as silylated selenides such as PhSeTMS and HMDSS toward epoxides. The present reactivity is also observed on using ILs as reaction media.
Tetrabutylammonium phenoxide induced reaction of silyl nucleophiles / A. Capperucci; C. Tiberi; S. Pollicino; A. Degl'Innocenti. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 50:(2009), pp. 2808-2810. [10.1016/j.tetlet.2009.03.167]
Tetrabutylammonium phenoxide induced reaction of silyl nucleophiles
CAPPERUCCI, ANTONELLA;DEGL'INNOCENTI, ALESSANDRO
2009
Abstract
Reaction of silyl dithiolanes with electrophiles can be efficiently promoted by catalytic amounts of tetrabutylammonium phenoxide (PhONn–Bu4), leading to a convenient access to functionalized dithiolanes. PhONn–Bu4 proved effective also in promoting reactions of silylated sulfides such as PhSTMS and HMDST as well as silylated selenides such as PhSeTMS and HMDSS toward epoxides. The present reactivity is also observed on using ILs as reaction media.
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