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Functionalization of closo ‐Borates via Iodonium Zwitterions
Author(s) -
Kaszyński Piotr,
Ringstrand Bryan
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201411858
Subject(s) - sulfonium , chemistry , surface modification , pyridinium , nucleophile , boron , thiol , combinatorial chemistry , zwitterion , medicinal chemistry , organic chemistry , molecule , salt (chemistry) , catalysis
A simple method for the functionalization of closo ‐borates [ closo ‐B 10 H 10 ] 2− ( 1 ), [ closo ‐1‐CB 9 H 10 ] − ( 2 ), [ closo ‐B 12 H 12 ] 2− ( 3 ), [ closo ‐1‐CB 11 H 12 ] − ( 4 ), and [3,3′‐Co(1,2‐C 2 B 9 H 11 ) 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.