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Hydroxyselenylation and Tethered Silanoxyselenylation of Allylic Silanols.

ABSTRACT: 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.

SUBMITTER: Joshi H

PROVIDER: S-EPMC8976763 | biostudies-literature | 2022 Apr

REPOSITORIES: biostudies-literature

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Hydroxyselenylation and Tethered Silanoxyselenylation of Allylic Silanols.

Joshi Harshit H Sathyamoorthi Shyam S

The Journal of organic chemistry 20220316 7

We present protocols for the highly regioselective hydroxyselenylation and silanoxyselenylation of allylic silanols. <i>N</i>-(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 con ...[more]

PMID: 35294203

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