Stable triorganoiodine complexes
4 affiliations
- 1La Trobe Institute for Molecular Science
- 2La Trobe University
- 3School of Chemistry
- 4Monash University
Abstract
The first examples of air stable acyclic triorganoiodine compounds, phenyliodine bis(1-(2-R)-o-carborane)s have been isolated from reactions of PhIL2 reagents with lithio-o-carboranes and crystallographically characterized. When R = H or Si(CH3)3, the complexes are predisposed to form o-carboryne through β-elimination as confirmed by a trapping reaction with naphthalene, where the R = H variant degrades during formation. The latter Si(CH3)3 derivative is isolable in modest yield, while for R = CH3, the resulting phenyliodine bis(1-(2-methyl)-o-carborane)s can be obtained in high yields. The complexes known so far appear to behave as nonnucleophilic bases, and treatment with strong protic acids affords more electrophilic phenyl(1-o-carboranyl) iodonium salts. Compared with our previous synthesis of an aryl(1-o-carboranyl) iodonium salt, this method is simpler and offers broadened scope. Less is known of these salts than previously assumed as earlier reports have now also been found incorrect. A preliminary study finds they can either arylate or 1-o-carboranylate a chloride nucleophile with chemoselectivity tuneable by electronic modification of the oCb ligand, providing a rare example of an o-carborane C atom reacting as an electrophile.
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BibTeX
@misc{sceney2026stable,
title = {{Stable triorganoiodine complexes}},
author = {Marcus Sceney and Harini A. Sivakumar and David R. Turner and Keith F. White and Jason L. Dutton},
howpublished = {ChemRxiv},
year = {2026},
month = oct,
doi = {10.26434/chemrxiv.15010513/v1},
url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010513/v1},
note = {CC BY},
}
RIS
TY - UNPB
TI - Stable triorganoiodine complexes
AU - Marcus Sceney
AU - Harini A. Sivakumar
AU - David R. Turner
AU - Keith F. White
AU - Jason L. Dutton
PY - 2026
DA - 2026/10/15
PB - ChemRxiv
DO - 10.26434/chemrxiv.15010513/v1
UR - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010513/v1
AB - The first examples of air stable acyclic triorganoiodine compounds, phenyliodine bis(1-(2-R)-o-carborane)s have been isolated from reactions of PhIL2 reagents with lithio-o-carboranes and crystallographically characterized. When R = H or Si(CH3)3, the complexes are predisposed to form o-carboryne through β-elimination as confirmed by a trapping reaction with naphthalene, where the R = H variant degrades during formation. The latter Si(CH3)3 derivative is isolable in modest yield, while for R = CH3, the resulting phenyliodine bis(1-(2-methyl)-o-carborane)s can be obtained in high yields. The complexes known so far appear to behave as nonnucleophilic bases, and treatment with strong protic acids affords more electrophilic phenyl(1-o-carboranyl) iodonium salts. Compared with our previous synthesis of an aryl(1-o-carboranyl) iodonium salt, this method is simpler and offers broadened scope. Less is known of these salts than previously assumed as earlier reports have now also been found incorrect. A preliminary study finds they can either arylate or 1-o-carboranylate a chloride nucleophile with chemoselectivity tuneable by electronic modification of the oCb ligand, providing a rare example of an o-carborane C atom reacting as an electrophile.
ER -