ao9b00643_si_001.pdf (2.38 MB)
Chemoselective Transformations of Aromatic Methoxymethyl Ethers Using Trialkylsilyl Triflate and 2,2′-Bipyridyl
journal contribution
posted on 2019-05-14, 08:14 authored by Mizushi Yanagihara, Reiya Ohta, Kenichi Murai, Mitsuhiro Arisawa, Hiromichi FujiokaAromatic methoxymethyl
(MOM) ethers behave differently from aliphatic
MOM ethers upon treatment with trialkylsilyl triflate (R3SiOTf) and 2,2′-bipyridyl. The aromatic MOM ethers are first
converted to silyl ethers and subsequently deprotected by hydrolysis
to give the mother alcohols when the R3SiOTf used is trimethylsilyl
triflate (TMSOTf). Conversely, direct conversion of aromatic MOM ethers
to aromatic triethylsilyl (TES) ethers is possible when the R3SiOTf used is triethylsilyl triflate (TESOTf).