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Synthesis 2021; 53(24): 4678-4681
DOI: 10.1055/a-1558-9135
DOI: 10.1055/a-1558-9135
paper
HMPA-Free Generation of Trialkylsilyllithium Reagents and Its Applications to the Synthesis of Silylboronic Esters
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
- Supporting information for this article is available online at https://doi.org/10.1055/a-1558-9135.
- Supporting Information
- CIF File
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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For reviews on the chemistry of silylboronic esters, see:
For transition-metal-catalyzed Si–H borylation of silanes, see:
For Me3Si–SiMe3, see:
For other Si–Si bond cleavage reactions, see:
For biological effects of HMPA, see:
A small number of reactions employing HMPA surrogates have been reported, see: