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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.
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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: