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

Tomomi Shimizu | Zendy; Shogo Morisako | Zendy; Yohsuke Yamamoto | Zendy; Atsushi Kawachi | Zendy

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

Author(s) -

Tomomi Shimizu,

Shogo Morisako,

Yohsuke Yamamoto,

Atsushi Kawachi

Publication year - 2019

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.9b03784

Subject(s) - intramolecular force , group (periodic table) , medicinal chemistry , chemistry , bond , stereochemistry , organic chemistry , business , finance

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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