Unsymmetrical Diaryliodonium Salts as Aryne Synthons: Renaissance of a C–H Deprotonative Approach to Arynes
A regio- and chemoselective C-H deprotonative strategy toward arynes is described that employs a hypervalent iodine leaving group. The unsymmetrical aryl(mesityl)iodonium salts used as aryne precursors are readily synthesized from commercially available aryl iodide and arylboronic acid building blocks. The bases LiHMDS and NaOt-Bu engage the diaryliodonium salts in a deprotonation event at an aromatic C-H bond and the transient arynes react in cycloaddition reactions with furan and benzyl azide or nucleophilic addition reaction with alicy-clic amines. The auxiliary component of aryl(auxiliary)iodonium salts can be sterically tuned to influence the regioselectivity of the C-H deprotonation event for meta-substituted aryl groups. 1 Introduction 2 Iodonium Salts as Aryne Precursors 3 Reaction Discovery and Optimization 4 Reaction Scope 5 Auxiliary-Controlled Regioselective Deprotonation 6 Beyond Cycloaddition with Furan 7 Conclusions and Outlook.
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Stuart D.R. 2016. Unsymmetrical Diaryliodonium Salts as Aryne Synthons: Renaissance of a C–H Deprotonative Approach to Arynes. Synlett, 28(3).