Bioorganic & Medicinal Chemistry Letters 2006-12-15

Allyl and benzyl iodides by the anomalous action of iodotrimethylsilane.

Qing Zhu, Matthew S Tremblay

Index: Bioorg. Med. Chem. Lett. 16 , 6170, (2006)

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Abstract

Iodotrimethylsilane (TMSI), routinely used for the dealkylation of ethers and esters, has been found to efficiently convert allyl and benzyl phosphotriesters into the corresponding iodides under mild, Brønsted-neutral conditions. In contrast, alkyl and aryl phosphotriesters were dealkylated to the corresponding phosphates under identical conditions.