Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

An Admix Approach To Determine Counter Anion Effects on Metal-Free Arylation Reactions with Diaryliodonium Salts

An Admix Approach To Determine Counter Anion Effects on Metal-Free Arylation Reactions with Diaryliodonium Salts
David R. Stuart, Thomas L. Seidl
A method to determine the effect of counter anions in metal-free arylation reactions of diaryliodonium salts is described. This approach avoids the independent synthesis of individual diaryliodonium salts and potentially enables assessment of a large number of different counter anions, including those that are synthetically challenging to install. Diaryliodonium tosylate salts serve as a general precursor for this approach, and an azide arylation reaction was used to develop this strategy. Further optimization and representative scope of azide arylation is demonstrated in yields that range from 74–95% (89% average). The use of this method as a screening tool has also been validated with arylation reactions of three different nucleophiles employing diphenyliodonium tosylate.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01599

DOI: 10.1021/acs.joc.7b01599

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