Intramolecular Activation of C–O Bond by an o-Boryl Group in o-(Alkoxysilyl)(diarylboryl)benzenes

[Image: see text] Halogen–lithium exchange reaction of o-(silyl)bromobenzene 5 with tert-BuLi afforded o-(silyl)lithiobenzene 6, which was reacted with (alkoxy)diarylboranes 7 to form borate intermediates 8. Treatment of 8 with chlorotrimethylsilane formed o-(alkoxysilyl)(diarylboryl)benzenes 4. The...

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Autores principales: Shimizu, Tomomi, Morisako, Shogo, Yamamoto, Yohsuke, Kawachi, Atsushi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6964514/
https://www.ncbi.nlm.nih.gov/pubmed/31956839
http://dx.doi.org/10.1021/acsomega.9b03784
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author Shimizu, Tomomi
Morisako, Shogo
Yamamoto, Yohsuke
Kawachi, Atsushi
author_facet Shimizu, Tomomi
Morisako, Shogo
Yamamoto, Yohsuke
Kawachi, Atsushi
author_sort Shimizu, Tomomi
collection PubMed
description [Image: see text] Halogen–lithium exchange reaction of o-(silyl)bromobenzene 5 with tert-BuLi afforded o-(silyl)lithiobenzene 6, which was reacted with (alkoxy)diarylboranes 7 to form borate intermediates 8. Treatment of 8 with chlorotrimethylsilane formed o-(alkoxysilyl)(diarylboryl)benzenes 4. The C–O bond in 4 was activated by intramolecular interaction between the oxygen atom and the boron atom. 4a readily reacted with MeOH and EtOH to afford the corresponding alkoxysilanes 10 and 11, respectively. Treatment of 10 with 1,4-diazabicyclo[2.2.2]octane (DABCO) afforded the silyloxyborate complex 13.
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spelling pubmed-69645142020-01-17 Intramolecular Activation of C–O Bond by an o-Boryl Group in o-(Alkoxysilyl)(diarylboryl)benzenes Shimizu, Tomomi Morisako, Shogo Yamamoto, Yohsuke Kawachi, Atsushi ACS Omega [Image: see text] Halogen–lithium exchange reaction of o-(silyl)bromobenzene 5 with tert-BuLi afforded o-(silyl)lithiobenzene 6, which was reacted with (alkoxy)diarylboranes 7 to form borate intermediates 8. Treatment of 8 with chlorotrimethylsilane formed o-(alkoxysilyl)(diarylboryl)benzenes 4. The C–O bond in 4 was activated by intramolecular interaction between the oxygen atom and the boron atom. 4a readily reacted with MeOH and EtOH to afford the corresponding alkoxysilanes 10 and 11, respectively. Treatment of 10 with 1,4-diazabicyclo[2.2.2]octane (DABCO) afforded the silyloxyborate complex 13. American Chemical Society 2019-12-30 /pmc/articles/PMC6964514/ /pubmed/31956839 http://dx.doi.org/10.1021/acsomega.9b03784 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 Shimizu, Tomomi
Morisako, Shogo
Yamamoto, Yohsuke
Kawachi, Atsushi
Intramolecular Activation of C–O Bond by an o-Boryl Group in o-(Alkoxysilyl)(diarylboryl)benzenes
title Intramolecular Activation of C–O Bond by an o-Boryl Group in o-(Alkoxysilyl)(diarylboryl)benzenes
title_full Intramolecular Activation of C–O Bond by an o-Boryl Group in o-(Alkoxysilyl)(diarylboryl)benzenes
title_fullStr Intramolecular Activation of C–O Bond by an o-Boryl Group in o-(Alkoxysilyl)(diarylboryl)benzenes
title_full_unstemmed Intramolecular Activation of C–O Bond by an o-Boryl Group in o-(Alkoxysilyl)(diarylboryl)benzenes
title_short Intramolecular Activation of C–O Bond by an o-Boryl Group in o-(Alkoxysilyl)(diarylboryl)benzenes
title_sort intramolecular activation of c–o bond by an o-boryl group in o-(alkoxysilyl)(diarylboryl)benzenes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6964514/
https://www.ncbi.nlm.nih.gov/pubmed/31956839
http://dx.doi.org/10.1021/acsomega.9b03784
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