Two-Step Protocol for Iodotrimethylsilane-Mediated Deoxy-Functionalization of Alcohols
European Journal of Organic Chemistry(2021)
摘要
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.
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关键词
Alcohol,Deoxy functionalization,Iodotrimethylsilane,Nucleophilic substitution
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