1093350-32-3

Upstream product

• 13195-64-7 diisopropyl malonate 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 536-80-1 iodosylbenzene 
• 591-50-4 iodobenzene 

Downstream Products

• 1093350-38-9 diisopropyl 2-phenylcyclopropane-1,1-dicarboxylate 
• 1393841-64-9 1-(1,2-diphenylethoxy)-2,2,6,6-tetramethylpiperidine 
• 1198573-63-5 diisopropyl (2S)-2-phenylcyclopropane-1,1-dicarboxylate 

Relevant academic research and scientific papers

Generation of Aryl Radicals through Reduction of Hypervalent Iodine(III) Compounds with TEMPONa: Radical Alkene Oxyarylation

A novel method for selective generation of aryl radicals from diaryliodonium salts and iodanylidene malonates with sodium 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPONa) as a single-electron transfer (SET) reducing reagent is described. In the presence of various alkenes, aryl radicals formed after SET-reduction of hypervalent iodine compounds undergo alkene addition and the adduct radicals that are thus generated are efficiently trapped by the concomitantly generated TEMPO radical to eventually afford oxyarylated products in moderate to very good yields. The efficiency of aryl radical generation of various iodine(III) reagents is studied and the generation of an iodanylidene malonate aryl radical is also investigated by computational methods.

General method for the synthesis of phenyliodonium ylides from malonate esters: Easy access to 1,1-cyclopropane diesters

(Chemical Equation Presented) A general method to access phenyliodonium ylides from malonates has been developed. These ylides provide easy access to a variety of useful 1,1-cyclopropane diesters using rhodium or copper catalysis. Moreover, the iodonium ylide of dimethyl malonate was obtained in 78% yield using improved conditions that involve a simple filtration step to isolate the desired product. This ylide was shown to be a safer and convenient alternative to the corresponding diazo compound and a very efficient way to 1,1-cyclopropane diesters when used with a catalytic amount of Rh2(esp)2.