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
