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2015 1

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Claisen rearrangement 1

allylation 1

fluoroalcohol 1

heterocycles 1

hypervalent iodine 1

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Fluoroalcohol-mediated reductive iodonio-Claisen rearrangement: Synthesis of complex

Hem Raj Khatri,Hai Nguyen,James K. Dunaway,Jianglong Zhu

Frontiers of Chemical Science and Engineering 2015, Volume 9, Issue 3, Pages 359-368 doi: 10.1007/s11705-015-1530-6

Abstract: Reductive iodonio-Claisen rearrangement (RICR) involving -iodanes and allyl or substituted-allyl silanes in fluoroalcohols, such as 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) and 2,2,2-trifluoroethanol (TFE), was studied for the synthesis of complex -allyl or substituted-allyl iodoarenes. In comparison to the previously reported condition involving boron trifluoride diethyl etherate, the RICR mediated by fluoroalcohols was found to proceed more effectively. The resulting complex -allyl iodoarenes are useful synthetic intermediates and can be readily converted to various heterocyclic compounds.

Keywords： hypervalent iodine allylation fluoroalcohol Claisen rearrangement heterocycles