The Journal of Organic Chemistry

Exchange of carbon ligands at iodine in iodonium salts. A direct synthesis of aryl (2-furyl) iodonium tosylates from aryl (tert-butylethynyl) iodonium tosylates

AJ Margida, GF Koser

Index: Margida, Anthony J.; Koser, Gerald F. Journal of Organic Chemistry, 1984 , vol. 49, p. 4703 - 4706

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Citation Number: 55

Abstract

Various [hydroxy (tosyloxy) iodo] arenes (RC6H41 (OH) OTs, R= H, 2-Me, 3-Me, 4-Me, 2-F, 3- F, 4-F, 2-C1, 3-C1) have been found to react with tert-butylacetylene in chloroform under reflux to give the corresponding aryl-(tert-butylethyny1) iodonium tosylates (Me3CC= cI+ C6H4R-OTs) in yields ranging from 56% to 80%. When the arylethynyl salts (R= 2-Me, 3-Me, 4-Me, 2-F, 3-F 4-F, 3-C1) were mixed with 2-lithiofuran in ether-hexane and treated ...