ol6b02818_si_001.pdf (6.53 MB)
Diacyl Disulfide: A Reagent for Chemoselective Acylation of Phenols Enabled by 4‑(N,N‑Dimethylamino)pyridine Catalysis
journal contribution
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 TanA 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.