3 years ago

Tris(trimethylsilyl)silylboronate Esters: Novel Bulky, Air- and Moisture-Stable Silylboronate Ester Reagents for Boryl Substitution and Silaboration Reactions

Tris(trimethylsilyl)silylboronate Esters: Novel Bulky, Air- and Moisture-Stable Silylboronate Ester Reagents for Boryl Substitution and Silaboration Reactions
Hajime Ito, Tomohiro Seki, Ryosuke Shishido, Eiji Yamamoto
New, bulky tris(trimethylsilyl)silylboronate pinacol and hexylene glycol esters ((TMS)3Si–B(pin) and (TMS)3Si–B(hg)) were prepared in 46 and 61% yields, respectively, by the reaction of tris(trimethylsilyl)silylpotassium with the corresponding boron electrophiles. Notably, these silylboronate esters exhibited high stability to air and silica gel and were applied to the transition-metal-free boryl substitution of aryl halides, providing the desired borylated products in high yields with excellent B:Si ratios (up to 96% yield, B/Si = 99/1). These new silylboronate esters were also applied to a sequential borylation/cross-coupling process with various aryl halides, as well as the base-mediated silaboration of styrene.

Publisher URL: http://dx.doi.org/10.1021/acs.organomet.7b00476

DOI: 10.1021/acs.organomet.7b00476

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