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Synthesis 2022; 54(22): 5003-5016
DOI: 10.1055/a-1814-9853
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
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
Publikationsverlauf
Eingereicht: 16. März 2022
Angenommen nach Revision: 01. April 2022
Accepted Manuscript online:
01. April 2022
Artikel online veröffentlicht:
17. Mai 2022
© 2022. Thieme. All rights reserved
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