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Functionalization of closo ‐Borates via Iodonium Zwitterions
Author(s) -
Kaszyński Piotr,
Ringstrand Bryan
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201411858
Subject(s) - sulfonium , pyridinium , surface modification , chemistry , boron , nucleophile , thiol , zwitterion , combinatorial chemistry , medicinal chemistry , polymer 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.