Diacyl Disulfide: A Reagent for Chemoselective Acylation of Phenols Enabled by 4-(N,N-Dimethylamino)pyridine Catalysis
Hong-Xin Liu, Ya-Qian Dang, Yun-Fei Yuan, Zhi-Fang Xu, Sheng-Xiang Qiu* and Hai-Bo Tan*
*Program for Natural Products Chemical Biology, South China
Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, China, Email:
sxqiu
scbg.ac.cn, tanhaiboscbg.ac.cn
H.-X. Liu, Y.-Q. Dang, Y.-F. Yuan, Z.-F. Xu, S.-X. Qiu, H.-B. Tan, Org. Lett., 2016, 18, 5584-5587.
DOI: 10.1021/acs.orglett.6b02818
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Abstract
The use of diacyl disulfide as an acylation reagent enables an efficient ester formation under DMAP catalysis. A site-selective acylation of phenolic and primary aliphatic hydroxyl groups greatly expands the scope of protecting group chemistry. Diacyl disulfides offer excellent moisture tolerance, high efficiency, and potential in synthetic chemistry and biologically meaningful natural product modification.
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Key Words
acylation, benzoates, organocatalysis
ID: J54-Y2016
