期刊
MOLECULES
卷 20, 期 9, 页码 15862-15880出版社
MDPI AG
DOI: 10.3390/molecules200915862
关键词
aryne; bis-functionalization; halophenol; silver trifluoroacetate; regioselectivity
资金
- UIC (LAS AFS)
- National Science Foundation [CHE 1361620]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1361620] Funding Source: National Science Foundation
Trapping of arynes with various nucleophiles provides a range of heteroatom-functionalized arene derivatives, but the corresponding reaction with water does not provide phenol derivatives. Silver trifluroacetate (AgO2CCF3) can nicely solve this problem. It was found that in typical organic solvent, AgO2CCF3 readily reacts with arynes to generate trifluoroacetoxy organosilver arene intermediate, which, upon treating with silica gel, provides phenolic products. This protocol can be extended to the synthesis of -halofunctionalized phenol derivatives by simply adding NBS (N-bromosuccinimides) or NIS (N-iodosuccinimides) to the reaction along with silver trifluroacetate, which provided -bromo or -iodophenol derivatives in good yield. However, the similar reactions with NCS (N-chlorosuccinimides) afforded only the protonated product instead of the expected -chlorophenols derivatives. Interestingly, substrates containing silyl substituents on 1,3-diynes resulted in -halotrifluoroacetates rather than their hydrolyzed product. Additionally, trapping the same arynes with other oxygen-based nucleophiles containing silver counter cation, along with NXS (N-halosuccinimides), generated -halooxyfunctionalized products.
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