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Diacyl Disulfide: A Reagent for Chemoselective Acylation of Phenols Enabled by 4‑(N,N‑Dimethylamino)pyridine Catalysis

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posted on 2016-10-21, 13:15 authored by Hong-Xin Liu, Ya-Qian Dang, Yun-Fei Yuan, Zhi-Fang Xu, Sheng-Xiang Qiu, Hai-Bo Tan
A general and excellent acylation reagent, diacyl disulfide, was uncovered for efficient ester formation enabled by DMAP (4-(N,N-dimethylamino)­pyridine) catalysis. This protocol offered a promising synthetic platform on site-selective acylation of phenolic and primary aliphatic hydroxyl groups, which greatly expanded the realm of protecting group chemistry. The importance of the reagent was also reflected by its excellent moisture tolerance, high efficiency, and potential in synthetic chemistry and biologically meaningful natural product modification.

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