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- W4380887586 abstract "Here, we document the reinvention of aryne chemistry with “old” o-diiodoarenes as aryne progenitors. We have established a NaH-mediated activation strategy for the generation of highly reactive aryne species in a controlled manner. The resulting arynes can efficiently participate in a C–C σ-bond-insertion reaction with unactivated ketones, which is difficult to achieve by existing methods. Density functional theory (DFT) calculations reveal that the two adjacent iodines in o-diiodoarenes play critical roles in the formation of aryne. The nucleophilic attack of hydride to the electrophilic iodine requires that the adjacent iodine act as a directing group to accelerate this process, whereas mono-substituted iodobenzene lacking the neighboring-group participation makes it difficult. The in-situ-formed enolates from ketones are proposed to adopt tetrameric aggregates to react with arynes, which accounts for the high regiochemistry for substrates with bulky substituents." @default.
- W4380887586 created "2023-06-17" @default.
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- W4380887586 date "2023-09-01" @default.
- W4380887586 modified "2023-10-16" @default.
- W4380887586 title "Direct insertion into the C–C bond of unactivated ketones with NaH-mediated aryne chemistry" @default.
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- W4380887586 doi "https://doi.org/10.1016/j.chempr.2023.05.032" @default.
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