title: A Selective C-H Deprotonation Strategy to Access Functionalized Arynes by Using Hypervalent Iodine.
abstract: Described here is an efficient method to access highly functionalized arynes from unsymmetrical aryl(mesityl)iodonium tosylate salts. The iodonium salts are prepared in a single pot from either commercially available aryl iodides or arylboronic acids. The aryne intermediates are generated by ortho-C-H deprotonation of aryl(mesityl)iodonium salt with a commercially available amide base and trapped in a cycloaddition reaction with furan in moderate to good yields. Coupling partners for the aryne intermediates beyond furan are also described, including benzyl azide and alicyclic amine nucleophiles. The regio- and chemoselectivity of this reaction is discussed and evidence for the spectator aryl ligand of the iodonium salt as a critical control element in selectivity is presented.
authors.affiliation: Department of Chemistry, Portland State University, Portland, OR, 97201, USA.
authors.forename: Sunil K
authors.initials: SK
authors.lastname: Sundalam
authors.affiliation: Department of Chemistry, Portland State University, Portland, OR, 97201, USA.
authors.forename: Aleksandra
authors.initials: A
authors.lastname: Nilova
authors.affiliation: Department of Chemistry, Portland State University, Portland, OR, 97201, USA.
authors.forename: Thomas L
authors.initials: TL
authors.lastname: Seidl
authors.affiliation: Department of Chemistry, Portland State University, Portland, OR, 97201, USA. dstuart@pdx.edu.
authors.forename: David R
authors.initials: DR
authors.lastname: Stuart
keywords: arynes; cycloaddition; hypervalent compounds; regioselectivity; synthetic methods