4.5 Article

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

Journal

SYNTHESIS-STUTTGART
Volume 53, Issue 24, Pages 4678-4681

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/a-1558-9135

Keywords

trialkylsilyllithium; hexaalkyldisilane; silylboronic ester; TPPA; HMPA

Funding

  1. JSPS fellowship for young scientists, JSPS KAKENHI [JP20J14589]

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Trialkylsilyllithium species can be easily generated under specific conditions and trapped by boron electrophiles. This method allows for the preparation of silylboronic esters.
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 Me-3 Si-B(pin).

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