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Hypervalent Iodine Reagent Useful for the Chemical Synthesis of Diatomic Carbon

Trimethylsilylethynyl(phenyl)iodonium tetrafluoroborate (1) has been reported as a precursor to ethynyl(phenyl)iodonium tetrafluoroborate (2), which is useful for the α-ethynylation of β-dicarbonyl compounds.1)

Miyamoto and Uchiyama et al. reported that treating 1 with tetrabutylammonium fluoride or cesium fluoride generates diatomic carbon (C2) at room temperature, which can be trapped by 9,10-dihydroanthracene or galvinoxyl free radical.2) They also demonstrated that C2 can be used as a molecular element for the bottom-up synthesis of nanocarbons. Another group has reported the synthesis of N-(acyloxy)ynamides using this method.3) A computational study suggested potential alternative pathways to form trapped compounds that do not involve free C2.4) Although both computational and experimental studies have been conducted, no definitive conclusions have been reached.5) Thus, 1 has been attracting attention not only for ethynylation reactions but also for studies in C2 chemical synthesis and its applications.

Hypervalent Iodine Reagent Useful for the Chemical Synthesis of Diatomic Carbon

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References

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