Chemoselective Transformations of Aromatic Methoxymethyl Ethers Using Trialkylsilyl Triflate and 2,2'-Bipyridyl

Mizushi Yanagihara; Reiya Ohta; Kenichi Murai; Mitsuhiro Arisawa; Hiromichi Fujioka

doi:10.1021/acsomega.9b00643

Chemoselective Transformations of Aromatic Methoxymethyl Ethers Using Trialkylsilyl Triflate and 2,2'-Bipyridyl

ACS Omega. 2019 May 14;4(5):8465-8471. doi: 10.1021/acsomega.9b00643. eCollection 2019 May 31.

Authors

Mizushi Yanagihara¹, Reiya Ohta¹, Kenichi Murai¹, Mitsuhiro Arisawa¹, Hiromichi Fujioka¹

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871, Japan.

Abstract

Aromatic 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).