115152-08-4

Upstream product

• 4636-16-2 iodoacetophenone 
• 2712-78-9 bis-[(trifluoroacetoxy)iodo]benzene 
• 536-74-3 phenylacetylene 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 3757-88-8 tributylstannylethynylbenzene 
• 1402548-38-2 phenyl(phenylethynyl)iodonium 2,2,2-trifluoroacetate 
• 57957-24-1 N-(1-phenylvinyl)acetamide 
• 2923-18-4 sodium 2,2,2-trifluoroacetate 
• 70-11-1 α-bromoacetophenone 

Downstream Products

• 582-24-1 1-phenyl-2-hydroxyethanone 

Relevant academic research and scientific papers

Synthesis and reactivity of aryl(alkynyl)iodonium salts

The first practical, yet simple, preparation of aryl(alkynyl)iodonium trifluoroacetate salts is described. The generic nature of this synthetic method has allowed the production of a range of aryl(alkynyl)iodonium trifluoroacetate salts with independent variation of both the alkynyl and aryliodo groups in yields of 30-85 %. Application of these new reagents to the synthesis of a series of 2-arylfuro[3,2-c]pyridines (40-64 %) highlights the potential of this class of materials as precursors to bioactive heterocyclic structures. These experiments have also demonstrated that, in this case, the effect of the aryliodo group on the reaction is negligible.

PhI(OAc)2-promoted umpolung acetoxylation of enamides for the synthesis of α-acetoxy ketones

Umpolung is a fundamental concept in organic chemistry, which provides an alternative strategy for the synthesis of target compounds which were not easily accessible by conventional methods. Herein, a mild and efficient PhI(OAc)2-promoted umpolung acetoxylation reactions of enamides was developed for the synthesis of α-acetoxy ketones. The reaction tolerates a wide range of functional groups and affords α-acetoxy ketones in good to excellent yields. PhI(OAc)2 serves as a source of acetoxy in the reaction.

Oxidative Assistance in the Conversion of α-Iodoketones to α-Ketols

Treatment with bis(trifluoroacetoxy)iodobenzene (2) followed by hydrolysis converted five phenacyl iodides 1a-e to phenacyl alcohols 8a-d, 9 but failed to convert exo-3-iodonorbornan-2-one (10) and 2-iodocyclohexanone (11) to α-ketols.Iodinations by proposed intermediate trifluoroacetoxy iodide (5) were assumed to explain the formation of p-diiodobenzene (7) and 2-hydroxy-1-(3'-iodo-4'-methoxyphenyl)ethanone (9).

Reactions of Aryl Ketones and Coumarins with Iodine(III) Tris(trifluoroacetate)

The reaction of acetophenones with iodine(III) tris(trifluoroacetate) yields 3'- and/or 2-iodo derivatives, depending upon the substituent on the aromatic ring and the reaction conditions.The reaction was examinedby changing the molar ratio of acetophenone versus the reagent, reaction temperature, and solvent.In similar reactions flavanones and coumarins gave iodo derivatives in which iodine is incorporated at various positions orientated by the oxygen functions. 1,2-Diphenylethanone yields 2-hydroxy-2-(2-iodophenyl)-1-phenylethanone and 1-(2-iodophenyl)-2-phenylethanedione.The reactions of other aromatic ketones such as 9-xanthenone, 9-fluorenone, and anthrone also give iodo derivatives in moderate to good yields.The mechanisms for the iodination at the α-carbon to the carbonyl group have been discussed.