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Fluorinations of unsymmetrical diaryliodonium salts containing ortho-sidearms; influence of sidearm on selectivity.

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journal contribution
posted on 19.03.2021, 10:48 by Ahmed MH Abudken, Eric G Hope, Kuldip Singh, Alison M Stuart
Activated aromatics were reacted with two different fluoroidoane reagents 1 and 2 in the presence of triflic acid to prepare only the para-substituted diaryliodonium salts. With fluoroiodane 1 the unsymmetrical diaryliodonium salts contained an ortho-propan-2-ol sidearm, whereas the alcohol sidearm was eliminated to form an ortho-styrene sidearm in the reaction with fluoroiodane 2. Only the diaryliodonium salts containing a styrene sidearm were fluorinated successfully to deliver para-fluorinated aromatics in good yields.

History

Citation

Org. Biomol. Chem., 2020,18, 6140-6146

Author affiliation

School of Chemistry

Version

VoR (Version of Record)

Published in

Organic & biomolecular chemistry

Volume

18

Pagination

6140-6146

Publisher

Royal Society of Chemistry (RSC)

issn

1477-0520

eissn

1477-0539

Acceptance date

23/07/2020

Copyright date

2020

Available date

19/03/2021

Spatial coverage

England

Language

eng

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