Journal
SYNLETT
Volume 28, Issue 3, Pages 275-279Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1588683
Keywords
aryne; arylation; cycloaddition; heterocycles; iodine; nucleophilic addition; regioselectivity; chemoselectivity
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Funding
- Portland State University
- American Chemical Society Petroleum Research Fund [54405]
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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 alicyclic 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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