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

Eiji Yamamoto, Ryosuke Shishido, Tomohiro Seki, Hajime Ito

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)3019-3022
Number of pages4
JournalOrganometallics
Volume36
Issue number16
DOIs
Publication statusPublished - Aug 28 2017

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moisture
reagents
esters
Esters
Substitution reactions
Moisture
substitutes
halides
air
Air
Styrene
Boron
Silica Gel
cross coupling
silica gel
styrenes
Transition metals
glycols
boron
transition metals

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Tris(trimethylsilyl)silylboronate Esters : Novel Bulky, Air- and Moisture-Stable Silylboronate Ester Reagents for Boryl Substitution and Silaboration Reactions. / Yamamoto, Eiji; Shishido, Ryosuke; Seki, Tomohiro; Ito, Hajime.

In: Organometallics, Vol. 36, No. 16, 28.08.2017, p. 3019-3022.

Research output: Contribution to journalArticle

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abstract = "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.",
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AB - 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.

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