Hydroxyselenylation and Tethered Silanoxyselenylation of Allylic Silanols

Hydroxyselenylation and Tethered Silanoxyselenylation of Allylic Silanols

We present protocols for the highly regioselective hydroxyselenylation and silanoxyselenylation of allylic silanols. N-(Phenylseleno)­phthalimide acts as the selenylating agent for both transformations. Under basic conditions, hydroxyselenylation proceeds with >20:1 regioselectivity, and the prod...

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Veröffentlicht in:Journal of organic chemistry 2022-04, Vol.87 (7), p.5017-5028
Hauptverfasser: Joshi, Harshit, Sathyamoorthi, Shyam
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Sathyamoorthi, Shyam
description We present protocols for the highly regioselective hydroxyselenylation and silanoxyselenylation of allylic silanols. N-(Phenylseleno)­phthalimide acts as the selenylating agent for both transformations. Under basic conditions, hydroxyselenylation proceeds with >20:1 regioselectivity, and the products are valuable synthons for further transformations. We show that the silanol plays a critical role in maintaining the yield and regioselectivity of this reaction. Surprisingly, under acidic conditions, the hydroxyselenylation pathway is blocked, and products of a tethered silanoxyselenylation are exclusive.
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