Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 10, Pages 6429-6440Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c00290
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- Jingchu University of Technology [PY201902]
- Science and Technology Bureau in Jingmen [2019YDKY082]
- Hubei Provincial Department of Education [B2019212]
- Student Innovation and Entrepreneurship Training Programs [201811336030, KC2018030]
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Aluminum triiodide is harnessed by N,N-dimethylformamide dimethyl acetal (DMF-DMA) for the selective cleavage of ethers via neighboring group participation. 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.
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