title: Functionalization of closo-Borates via Iodonium Zwitterions.
abstract: A simple method for the functionalization of closo-borates [closo-B10 H10 ](2-) (1), [closo-1-CB9 H10 ](-) (2), [closo-B12 H12 ](2-) (3), [closo-1-CB11 H12 ](-) (4), and [3,3'-Co(1,2-C2 B9 H11 )2 ](-) (5) is described. Treatment of the anions and their derivatives with ArI(OAc)2 gave aryliodonium zwitterions, which were sufficiently stable for chromatographic purification. The reactions of these zwitterions with nucleophiles provided facile access to pyridinium, sulfonium, thiol, carbonitrile, acetoxy, and amino derivatives. The synthetic results are augmented by mechanistic considerations.
authors: Department of Chemistry, Vanderbilt University, Nashville, TN 37235 (USA). piotr.kaszynski@vanderbilt.edu.|Department of Chemistry, Middle Tennessee University, Murfreesboro, TN 37123 (USA). piotr.kaszynski@vanderbilt.edu.|Faculty of Chemistry, University of Łódź, Tamka 12, 91-403 Łódź (Poland). piotr.kaszynski@vanderbilt.edu.
authors: Piotr
authors: P
authors: Kaszyński
authors: Department of Chemistry, Vanderbilt University, Nashville, TN 37235 (USA).
authors: Bryan
authors: B
authors: Ringstrand
mesh_terms: D001881:Borates / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry*; D007477:Ions / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry; D013450:Sulfones / Q000737:chemistry
chemical_list: D001881:Borates; D007454:Iodides; D007477:Ions; D011725:Pyridines; D013438:Sulfhydryl Compounds; D013450:Sulfones; C023666:pyridine
keywords: closo-borates; cluster compounds; functionalization; iodonium zwitterions; synthetic methods