Synlett 2024; 35(08): 889-894
DOI: 10.1055/a-2198-3637
cluster
Special Issue dedicated to Keith Fagnou

Synthesis of Alkyl Aryl Ethers by O-Arylation of Alcohols with Diaryliodonium Salts: Scope, Limitations, and Mechanism

Rory T. Gallagher
,
Soocheta Jha
,
Bryan E. Metze
,
David R. Stuart
This work was partially supported by the National Science Foundation (NSF; grant number 2154500). The NSF also provided instrument funding for the BioAnalytical Mass Spectrometry Facility at PSU under grant number 1828753.


This manuscript is dedicated to the memory of Professor Keith Fagnou.

Abstract

We describe the development of a C–O coupling reaction between aryl(2,4,6-trimethoxyphenyl)iodonium salts and aliphatic alcohols under weak base conditions. The scope of the reaction is presented, with 16 examples ranging in yield from moderate to high (54–96%). The limitations of the reaction are also presented. Mechanistic experiments reveal a complex network of reactions that include side reactions that generate arynes and oxidize the alcohol nucleophile.

Supporting Information



Publication History

Received: 01 September 2023

Accepted after revision: 25 October 2023

Accepted Manuscript online:
25 October 2023

Article published online:
21 November 2023

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