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

Shintaro Kamio; Taiki Imagawa; Masaaki Nakamoto; Martin Oestreich; Hiroto Yoshida

doi:10.1055/a-1558-9135

Synthesis, Table of Contents

Synthesis 2021; 53(24): 4678-4681
DOI: 10.1055/a-1558-9135

paper

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

Authors

Shintaro Kamio

^aGraduate School of Advanced Science and Engineering, Hiroshima University, Higashi-Hiroshima 739-8526, Japan

^bInstitut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623 Berlin, Germany
Taiki Imagawa

^aGraduate School of Advanced Science and Engineering, Hiroshima University, Higashi-Hiroshima 739-8526, Japan
Masaaki Nakamoto

^aGraduate School of Advanced Science and Engineering, Hiroshima University, Higashi-Hiroshima 739-8526, Japan
Martin Oestreich ∗

^bInstitut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623 Berlin, Germany
Hiroto Yoshida ∗

^aGraduate School of Advanced Science and Engineering, Hiroshima University, Higashi-Hiroshima 739-8526, Japan

Abstract

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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).

Key words

trialkylsilyllithium - hexaalkyldisilane - silylboronic ester - TPPA - HMPA

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References

References

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