Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 22, Pages 6576-6581Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201411858
Keywords
closo-borates; cluster compounds; functionalization; iodonium zwitterions; synthetic methods
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Funding
- National Science Foundation [DMR-1207585]
- Direct For Mathematical & Physical Scien
- Division Of Materials Research [1207585] Funding Source: National Science Foundation
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A 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.
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