Biomaterial Database

Functionalization of closo-Borates via Iodonium Zwitterions. 2015

Piotr Kaszyński, and Bryan Ringstrand

Department of Chemistry, Vanderbilt University, Nashville, TN 37235 (USA). piotr.kaszynski@vanderbilt.edu.

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.

UI	MeSH Term	Description	Entries
D007454	Iodides	Inorganic binary compounds of iodine or the I- ion.	Iodide
D007477	Ions	An atom or group of atoms that have a positive or negative electric charge due to a gain (negative charge) or loss (positive charge) of one or more electrons. Atoms with a positive charge are known as CATIONS; those with a negative charge are ANIONS.
D011725	Pyridines	Compounds with a six membered aromatic ring containing NITROGEN. The saturated version is PIPERIDINES.
D001881	Borates	Inorganic or organic salts and esters of boric acid.	Borate
D013237	Stereoisomerism	The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D013438	Sulfhydryl Compounds	Compounds containing the -SH radical.	Mercaptan,Mercapto Compounds,Sulfhydryl Compound,Thiol,Thiols,Mercaptans,Compound, Sulfhydryl,Compounds, Mercapto,Compounds, Sulfhydryl
D013450	Sulfones		Sulfone