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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Detalles Bibliográficos
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
Descripción
Sumario:[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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