Organic Chemistry

HMPA-Free Generation of Trialkylsilyl Lithium Reagents and Its Application to Synthesis of Silylboronic Esters

Hiroto Yoshida Graduate School of Advanced Science and Engineering, Hiroshima University


Trialkylsilyl lithium species have turned out to be facilely generated by treating hexaalkyl disilanes with methyl lithium 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).


Thumbnail image of ChemRxiv.pdf
download asset ChemRxiv.pdf 0.64 MB [opens in a new tab]

Supplementary material

Thumbnail image of ChemRxivSI.pdf
download asset ChemRxivSI.pdf 0.49 MB [opens in a new tab]