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

[Image: see text] Aromatic methoxymethyl (MOM) ethers behave differently from aliphatic MOM ethers upon treatment with trialkylsilyl triflate (R(3)SiOTf) and 2,2′-bipyridyl. The aromatic MOM ethers are first converted to silyl ethers and subsequently deprotected by hydrolysis to give the mother alco...

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Autores principales: Yanagihara, Mizushi, Ohta, Reiya, Murai, Kenichi, Arisawa, Mitsuhiro, Fujioka, Hiromichi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6649284/
https://www.ncbi.nlm.nih.gov/pubmed/31459935
http://dx.doi.org/10.1021/acsomega.9b00643
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author Yanagihara, Mizushi
Ohta, Reiya
Murai, Kenichi
Arisawa, Mitsuhiro
Fujioka, Hiromichi
author_facet Yanagihara, Mizushi
Ohta, Reiya
Murai, Kenichi
Arisawa, Mitsuhiro
Fujioka, Hiromichi
author_sort Yanagihara, Mizushi
collection PubMed
description [Image: see text] Aromatic methoxymethyl (MOM) ethers behave differently from aliphatic MOM ethers upon treatment with trialkylsilyl triflate (R(3)SiOTf) 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 R(3)SiOTf used is trimethylsilyl triflate (TMSOTf). Conversely, direct conversion of aromatic MOM ethers to aromatic triethylsilyl (TES) ethers is possible when the R(3)SiOTf used is triethylsilyl triflate (TESOTf).
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spelling pubmed-66492842019-08-27 Chemoselective Transformations of Aromatic Methoxymethyl Ethers Using Trialkylsilyl Triflate and 2,2′-Bipyridyl Yanagihara, Mizushi Ohta, Reiya Murai, Kenichi Arisawa, Mitsuhiro Fujioka, Hiromichi ACS Omega [Image: see text] Aromatic methoxymethyl (MOM) ethers behave differently from aliphatic MOM ethers upon treatment with trialkylsilyl triflate (R(3)SiOTf) 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 R(3)SiOTf used is trimethylsilyl triflate (TMSOTf). Conversely, direct conversion of aromatic MOM ethers to aromatic triethylsilyl (TES) ethers is possible when the R(3)SiOTf used is triethylsilyl triflate (TESOTf). American Chemical Society 2019-05-14 /pmc/articles/PMC6649284/ /pubmed/31459935 http://dx.doi.org/10.1021/acsomega.9b00643 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Yanagihara, Mizushi
Ohta, Reiya
Murai, Kenichi
Arisawa, Mitsuhiro
Fujioka, Hiromichi
Chemoselective Transformations of Aromatic Methoxymethyl Ethers Using Trialkylsilyl Triflate and 2,2′-Bipyridyl
title Chemoselective Transformations of Aromatic Methoxymethyl Ethers Using Trialkylsilyl Triflate and 2,2′-Bipyridyl
title_full Chemoselective Transformations of Aromatic Methoxymethyl Ethers Using Trialkylsilyl Triflate and 2,2′-Bipyridyl
title_fullStr Chemoselective Transformations of Aromatic Methoxymethyl Ethers Using Trialkylsilyl Triflate and 2,2′-Bipyridyl
title_full_unstemmed Chemoselective Transformations of Aromatic Methoxymethyl Ethers Using Trialkylsilyl Triflate and 2,2′-Bipyridyl
title_short Chemoselective Transformations of Aromatic Methoxymethyl Ethers Using Trialkylsilyl Triflate and 2,2′-Bipyridyl
title_sort chemoselective transformations of aromatic methoxymethyl ethers using trialkylsilyl triflate and 2,2′-bipyridyl
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6649284/
https://www.ncbi.nlm.nih.gov/pubmed/31459935
http://dx.doi.org/10.1021/acsomega.9b00643
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