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Missing Reactivity of Trimethylsilyl Reagents: Dehalogenative Activation Enabling One-Pot Generation of Aryne from 2-Iodophenol

03 April 2019, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Herein we present a missing reactivity of trimethylsilyl reagents; dehalogenative activation, which involves abstracting a halogen atom and anionically activating the substrate similar to the halogen-metal exchange reaction in classical carbanion species. This missing reactivity allowed for the one-pot generation of aryne from 2-iodophenol.

Keywords

exchanges
aryne reaction classes
aryne precursors

Supplementary materials

Title
Description
Actions
Title
190314-silicate-SI
Description
Actions

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Version History

Apr 03, 2019 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.7934987.v1
D O I: 10.26434/chemrxiv.7934987.v1 [opens in a new tab]

Funding

This study was partly supported by a Grant-in-Aid for Young Scientists (No. 17K14498, and 15K17863).

Author’s competing interest statement

There are no conflicts to declare.

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