Hydroxyselenylation and Tethered Silanoxyselenylation of Allylic Silanols [post]

2022 unpublished
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
more » ... , the hydroxyselenylation pathway is blocked, and products of a tethered silanoxyselenylation are exclusive.
doi:10.26434/chemrxiv-2022-xx1zg fatcat:znbuw3t62ffxzpcvdqptgxmwcy