Fluoroalcohol-mediated reductive iodonio-Claisen rearrangement： Synthesis of complex ortho-substituted-allyl iodoarenes  

作　　者：Hem Raj Khatri Hai Nguyen James K. Dunaway Jianglong Zhu 

机构地区：[1]Department of Chemistry and Biochemistry and School of Green Chemistry and Engineering, The University of Toledo, Toledo, OH 43606, USA

出　　处：《Frontiers of Chemical Science and Engineering》2015年第3期359-368,共10页化学科学与工程前沿（英文版）

摘　　要：Reductive iodonio-Claisen rearrangement （RICR） involving 23-iodanes and allyl or substituted-allyl silanes in fluoroalcohols, such as 1,1,1,3,3,3-hexafluoroi- sopropanol （HFIP） and 2,2,2-trifluoroethanol （TFE）, was studied for the synthesis of complex ortho-allyl or substituted-allyl iodoarenes. In comparison to the pre- viously reported condition involving boron trifluoride diethyl etherate, the RICR mediated by fluoroalcohols was found to proceed more effectively. The resulting complex ortho-allyl iodoarenes are useful synthetic intermediates and can be readily converted to various heterocyclic compounds.Reductive iodonio-Claisen rearrangement （RICR） involving 23-iodanes and allyl or substituted-allyl silanes in fluoroalcohols, such as 1,1,1,3,3,3-hexafluoroi- sopropanol （HFIP） and 2,2,2-trifluoroethanol （TFE）, was studied for the synthesis of complex ortho-allyl or substituted-allyl iodoarenes. In comparison to the pre- viously reported condition involving boron trifluoride diethyl etherate, the RICR mediated by fluoroalcohols was found to proceed more effectively. The resulting complex ortho-allyl iodoarenes are useful synthetic intermediates and can be readily converted to various heterocyclic compounds.

关 键 词：hypervalent iodine ALLYLATION FLUOROALCOHOL Claisen rearrangement HETEROCYCLES 

分 类 号：TQ225.52[化学工程—有机化工] O621.262[理学—有机化学]