A Selective C-H Deprotonation Strategy to Access Functionalized Arynes by Using Hypervalent Iodine
We acknowledge Portland State University and the donors ofthe American Chemical Society Petroleum Research Fund(PRF DNI1 #54405) for support of this research.
Described here is an efficient method to accesshighly functionalizedarynes from unsymmetrical aryl-(mesityl)iodonium tosylate salts.The iodonium salts areprepared in asingle pot from either commercially availablearyl iodides or arylboronic acids.The aryne intermediates aregenerated by ortho-C¢Hdeprotonation of aryl-(mesityl)iodonium salt with acommercially available amidebase and trapped in acycloaddition reaction with furan inmoderate to good yields.Coupling partners for the aryneintermediates beyond furan are also described, includingbenzyl azide and alicyclic amine nucleophiles.The regio-and chemoselectivity of this reaction is discussed and evidencefor the spectator aryl ligand of the iodonium salt as acriticalcontrol element in selectivity is presented.
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Sundalam, S. K., Nilova, A., Seidl, T. L., & Stuart, D. R. (2016). A Selective C− H Deprotonation Strategy to Access Functionalized Arynes by Using Hypervalent Iodine. Angewandte Chemie International Edition.