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dc.contributor.authorKarmakar, R.
dc.contributor.authorGhorai, S.
dc.contributor.authorXia, Y. Z.
dc.contributor.authorLee, D.
dc.date.accessioned2016-08-29T16:33:09Z
dc.date.available2016-08-29T16:33:09Z
dc.date.issued2015-09-01
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/10027/21096
dc.descriptionThis is a copy of an article published in the Molecules. www.mdpi.com/journal/molecules. ©2015 Karmakar, Rajdip, et al.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).en_US
dc.language.isoen_USen_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 Surrogateen_US
dc.typeArticleen_US


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