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dc.contributor.authorKarmakar, R
dc.contributor.authorGhorai, S
dc.contributor.authorXia, Y
dc.contributor.authorLee, D
dc.date.accessioned2016-05-04T22:25:11Z
dc.date.available2016-05-04T22:25:11Z
dc.date.issued2015-08-31
dc.identifier.bibliographicCitationKarmakar, R., Ghorai, S., Xia, Y. Z. and Lee, D. Synthesis of Phenolic Compounds by Trapping Arynes with a Hydroxy Surrogate. Molecules. 2015. 20(9): 15862-15880. DOI: 10.3390/molecules200915862.en_US
dc.identifier.issn1420-3049
dc.identifier.urihttp://hdl.handle.net/10027/20516
dc.descriptionThis is a copy of an article published in the Molecules © 2015 MDPI Publications.en_US
dc.description.abstractTrapping 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 α-halofunctionalized phenol derivatives by simply adding NBS (N-bromosuccinimides) or NIS (N-iodosuccinimides) to the reaction along with silver trifluroacetate, which provided α-bromo or α-iodophenol derivatives in good yield. However, the similar reactions with NCS (N-chlorosuccinimides) afforded only the protonated product instead of the expected α-chlorophenols derivatives. Interestingly, substrates containing silyl substituents on 1,3-diynes resulted in α-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 α-halooxyfunctionalized products.en_US
dc.description.sponsorshipFinancial support from UIC (LAS AFS) and the National Science Foundation (CHE 1361620) is greatly acknowledged.en_US
dc.publisherMDPIen_US
dc.subjectaryneen_US
dc.subjectbis-functionalizationen_US
dc.subjecthalophenolen_US
dc.subjectsilver trifluoroacetateen_US
dc.subjectregioselectivityen_US
dc.titleSynthesis of Phenolic Compounds by Trapping Arynes with a Hydroxy Surrogate.en_US
dc.typeArticleen_US


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