Synthesis of Phenolic Compounds by Trapping Arynes with a Hydroxy Surrogate

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Rajdip KarmakarDaesung Lee

Abstract

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 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.

References

Jan 12, 2010·Journal of the American Chemical Society·Paul H-Y CheongK N Houk
Feb 5, 2011·Biotechnology Advances·Silvia MartinsJose A Teixeira
Mar 1, 2011·Journal of the American Chemical Society·Sarah M BronnerNeil K Garg
Apr 13, 2011·Angewandte Chemie·Kevin M AllanBrian M Stoltz
Mar 17, 2012·Angewandte Chemie·Christian M Gampe, Erick M Carreira
Mar 27, 2012·Chemical Reviews·Pamela M Tadross, Brian M Stoltz
Aug 11, 2012·Journal of the American Chemical Society·Sarah M BronnerNeil K Garg
Oct 13, 2012·Nature·Thomas R HoyeBrian P Woods
Mar 13, 2013·Journal of the American Chemical Society·Sang Young YunDaesung Lee
Sep 19, 2014·Journal of the American Chemical Society·Patrick H WilloughbyThomas R Hoye
Oct 11, 2014·Journal of the American Chemical Society·Jose M MedinaK N Houk

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Citations

Mar 25, 2016·Journal of the American Chemical Society·Junhua ChenThomas R Hoye
Jan 21, 2016·Chemistry : a European Journal·Wenbo LiJunliang Zhang
Jan 27, 2016·Chemical Society Reviews·Rajdip Karmakar, Daesung Lee
Jan 24, 2019·The Journal of Organic Chemistry·Maggie ChenK N Houk

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Methods Mentioned

BETA
column chromatography

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