Two‐Step Protocol for Iodotrimethylsilane‐Mediated Deoxy‐Functionalization of Alcohols

We have developed a two‐step protocol for iodotrimethylsilane‐mediated deoxy‐functionalization of primary and secondary alcohols to afford products containing a C−N, C−S, or C−O bond. In the first step the alcohol undergoes iodination with iodotrimethylsilane, and in the second, the iodine atom is r...

Full description

Saved in:
Bibliographic Details
Published in:European journal of organic chemistry 2021-02, Vol.2021 (7), p.1179-1183
Main Authors: Chen, Yuming, He, Ru, Song, Hongjian, Yu, Guoqing, Li, Chenglin, Liu, Yuxiu, Wang, Qingmin
Format: Article
Language:English
Subjects:
Alcohol
Alcohols
Deoxy functionalization
Iodination
Iodine
Iodotrimethylsilane
Natural products
Nucleophiles
Nucleophilic substitution
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:We have developed a two‐step protocol for iodotrimethylsilane‐mediated deoxy‐functionalization of primary and secondary alcohols to afford products containing a C−N, C−S, or C−O bond. In the first step the alcohol undergoes iodination with iodotrimethylsilane, and in the second, the iodine atom is replaced by a N, S, or O nucleophile. Compared with traditional Mitsunobu reaction, non‐acidic pre‐nucleophiles can be used, and the reaction proceeds with retention of configuration. This operationally simple, highly efficient protocol can be used for some natural products and small‐molecule drugs containing hydroxy‐group. A two‐step protocol for iodotrimethylsilane‐mediated deoxy‐functionalization of primary and secondary alcohols was described. This protocol involves iodination of alcohol and then replaced by a N, S, or O nucleophile. Compared with traditional Mitsunobu reaction, non‐acidic pre‐nucleophiles can be used in this protocol and configuration of alcohols can be retained.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202001602