Ortho-Carborane-Supported Hypervalent Iodine(III) Reagents: A Scaffold for Enhanced Oxidative Capability

The first C-bound ortho-carborane (oCb) supported hypervalent iodine(III) -IL<sub>2</sub> type species are reported in RoCb-IL<sub>2</sub>, for L = F and OTf, including two structurally verified -IF<sub>2</sub> examples. Initial synthetic observations and supporting theoretical calculations suggest that the new oCb-IL<sub>2</sub> type compounds will be more reactive than any known Ar-IL<sub>2</sub> compound. This is exemplified by a previously unobserved oxidative demethylation of trimethylsilyl fluoride, suggesting that many substrates unreactive toward Ar-IL<sub>2</sub> could be susceptible to oxidation by oCb-IL<sub>2</sub>.

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Publication Details

Journal
Journal of the American Chemical Society
Published
2025-08-28
DOI
https://doi.org/10.1021/jacs.5c10358
Primary Topic
Boron Compounds in Chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

Ortho-Carborane-Supported Hypervalent Iodine(III) Reagents: A Scaffold for Enhanced Oxidative Capability

Jason L. Dutton, Keith F. White, Marcus Sceney
Journal of the American Chemical Society
Boron Compounds in Chemistry
article

Ortho-Carborane-Supported Hypervalent Iodine(III) Reagents: A Scaffold for Enhanced Oxidative Capability

Jason L. Dutton, Keith F. White, Marcus Sceney
article en

Abstract

The first C-bound ortho-carborane (oCb) supported hypervalent iodine(III) -IL<sub>2</sub> type species are reported in RoCb-IL<sub>2</sub>, for L = F and OTf, including two structurally verified -IF<sub>2</sub> examples. Initial synthetic observations and supporting theoretical calculations suggest that the new oCb-IL<sub>2</sub> type compounds will be more reactive than any known Ar-IL<sub>2</sub> compound. This is exemplified by a previously unobserved oxidative demethylation of trimethylsilyl fluoride, suggesting that many substrates unreactive toward Ar-IL<sub>2</sub> could be susceptible to oxidation by oCb-IL<sub>2</sub>.

Journal of the American Chemical SocietyVol. 147(36)
La Trobe University (AU), Institute for Molecular Science (JP)
Australian Research Council
Openalex Percentile: Top 68%
Boron Compounds in Chemistry
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Ortho-Carborane-Supported Hypervalent Iodine(III) Reagents: A Scaffold for Enhanced Oxidative Capability — Jason L. Dutton, Keith F. White, et al. · Journal of the American Chemical Society (2025) | TGRS Research Map | TGRS