Functionalization of closo‐Borates via Iodonium Zwitterions

Publisher: John Wiley & Sons Inc

E-ISSN: 1521-3773|54|22|6576-6581

ISSN: 1433-7851

Source: ANGEWANDTE CHEMIE INTERNATIONAL EDITION, Vol.54, Iss.22, 2015-05, pp. : 6576-6581

Disclaimer: Any content in publications that violate the sovereignty, the constitution or regulations of the PRC is not accepted or approved by CNPIEC.

Previous Menu Next

Abstract

AbstractA simple method for the functionalization of closo‐borates [closo‐B10H10]2− (1), [closo‐1‐CB9H10]− (2), [closo‐B12H12]2− (3), [closo‐1‐CB11H12]− (4), and [3,3′‐Co(1,2‐C2B9H11)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.