Regiocontrol by Halogen Substituent on Arynes: Generation of 3-Haloarynes and Their Synthetic Reactions

Hideto Miyabe

doi:10.1055/a-1814-9853

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(22): 5003-5016
DOI: 10.1055/a-1814-9853

special topic

Aryne Chemistry in Synthesis

Regiocontrol by Halogen Substituent on Arynes: Generation of 3-Haloarynes and Their Synthetic Reactions

Hideto Miyabe∗

Abstract

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Abstract

The use of arynes as highly reactive intermediates has attracted substantial attention in organic synthesis. To enhance the utility of arynes, the regiocontrol in the reactions of unsymmetrically substituted arynes is an important task. The introduction of halogen substituent at 3-position of arynes leads to sufficient regiocontrol for various synthetic reactions. This short review highlights the utility of 3-haloarynes in organic synthesis and discusses the distortion models used to explain regioselectivity, representative reactions of 3-haloarynes generated from polyhaloarenes, and the preparation and reactions of easily activatable aryne precursors.

1 Introduction

2 Distortion Models

3 Reaction of Precursors Activated by an Organometallic Reagent or Base

4 Preparation of Easily Activatable Precursors

5 Reactions of Easily Activatable Precursors

6 Concluding Remarks

Key words

aryne - 3-haloaryne - benzyne - halogen - regiocontrol - Fries rearrangement

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Referenzen

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