Synthesis 2021; 53(24): 4678-4681
DOI: 10.1055/a-1558-9135
paper

HMPA-Free Generation of Trialkylsilyllithium Reagents and Its Applications to the Synthesis of Silylboronic Esters

a   Graduate School of Advanced Science and Engineering, Hiroshima University, Higashi-Hiroshima 739-8526, Japan
b   Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623 Berlin, Germany
,
a   Graduate School of Advanced Science and Engineering, Hiroshima University, Higashi-Hiroshima 739-8526, Japan
,
a   Graduate School of Advanced Science and Engineering, Hiroshima University, Higashi-Hiroshima 739-8526, Japan
,
b   Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623 Berlin, Germany
,
a   Graduate School of Advanced Science and Engineering, Hiroshima University, Higashi-Hiroshima 739-8526, Japan
› Author Affiliations
JSPS fellowship for young scientists, JSPS KAKENHI Grant Number JP20J14589.


Abstract

Trialkylsilyllithium species have turned out to be facilely generated by treating hexaalkyldisilanes with methyllithium in the presence of tris(N,N-tetramethylene)phosphoric triamide (TPPA) as an activator, which can be trapped by boron electrophiles to afford silylboronic esters including long-awaited Me3Si–B(pin).

Supporting Information



Publication History

Received: 08 July 2021

Accepted after revision: 26 July 2021

Accepted Manuscript online:
26 July 2021

Article published online:
23 August 2021

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