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

ACS Omega

Department of Applied Chemistry, Graduate School of Science and Engineering and Department of Chemical Science and Technology, Faculty of Bioscience and Applied Chemistry, Hosei University, 3-7-2 Kajino-cho, Koganei, Tokyo 184-8584, Japan.

Published: January 2020

Halogen-lithium exchange reaction of -(silyl)bromobenzene with -BuLi afforded -(silyl)lithiobenzene , which was reacted with (alkoxy)diarylboranes to form borate intermediates . Treatment of with chlorotrimethylsilane formed -(alkoxysilyl)(diarylboryl)benzenes . The C-O bond in was activated by intramolecular interaction between the oxygen atom and the boron atom. readily reacted with MeOH and EtOH to afford the corresponding alkoxysilanes and , respectively. Treatment of with 1,4-diazabicyclo[2.2.2]octane (DABCO) afforded the silyloxyborate complex .

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6964514PMC
http://dx.doi.org/10.1021/acsomega.9b03784DOI Listing

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