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

07 June 2021, Version 1
Working Paper
This content is an early or alternative research output and has not been peer-reviewed by Cambridge University Press at the time of posting.

Abstract

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).

Keywords

silyl lithium reagents
silyl boronic esters

Supplementary materials

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Now Published

HMPA-Free Generation of Trialkylsilyllithium Reagents and Its Applications to the Synthesis of Silylboronic Esters [opens in a new tab]
Martin Oestreich, Hiroto Yoshida, Shintaro Kamio, Taiki Imagawa, Masaaki Nakamoto journal article
Synthesis , Volume 53, Issue 24
Online publication date: Aug 23, 2021

Version History

Jun 07, 2021 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv.14737362.v1
D O I: 10.26434/chemrxiv.14737362.v1 [opens in a new tab]

Funding

JSPS KAKENHI Grant Number JP20J14589

Author’s competing interest statement

There are no conflicts to declare.

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