Dayong Sang, Huaxin Yue, Zhengdong Zhao
Apr 22, 2020
Citations
0
Influential Citations
5
Citations
Journal
The Journal of organic chemistry
Abstract
Aluminum triiodide is tamed by N,N-dimethylformamide dimethyl acetal (DMF-DMA) for selective cleavage of ethers with the assistance of neighboring group participation effect. Various acid-labile functional groups, including carboxylate, allyl, tert-butyldimethylsilyl (TBS) and tert-butoxycarbonyl (Boc), suffer the conditions intact. The method offers an efficient approach to cleaving catechol monoalkyl ethers and to uncovering phenols from acetal-type protecting groups such as methoxymethyl (MOM), methoxyethoxymethyl (MEM) and tetrahydropyranyl (THP) chemoselectively.