European Journal of Organic Chemistry p. 1179 - 1183 (2021)
Update date:2022-08-03
Topics:
Chen, Yuming
He, Ru
Song, Hongjian
Yu, Guoqing
Li, Chenglin
Liu, Yuxiu
Wang, Qingmin
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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