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CAS 887144-97-0, Cat. No EN300-195971
Reagent for electrophilic trifluoromethylation

Togni reagent

This reagent is used for direct electrophilic trifluoromethylation of many nucleophiles[1], [2]. It is a white solid that is soluble in most organic solvents and has similar properties to the Togni II reagent[2]. As a Togni II reagent, it is capable of selective reaction with thiols to yield corresponding thioethers. However, this reagent is less reactive and offers a softer approach, has unique properties, and is mainly used for reactions with β-keto esters or α-nitro carbonyl compounds[1], [3]. Recently was developed a methodology for trifluoromethylarylation of alkenes with anilines and the title reagent, which offers good yields and utilizes no additives, transition metals, photocatalysts, or an excess of reagents[2]. While the Togni II reagent doesn’t undergo or give low yields with this methodology.

Synonyms: Trifluoromethyl-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole; 3,3-Dimethyl-1-(trifluoromethyl)-1,2-benziodoxole (ACI); 1-Trifluoromethyl-3,3-dimethyl-1,2-benziodoxole; 3,3-Dimethyl-1-trifluoromethyl-1,2-benzoiodoxole

Selected publication

  1. Novel 10‐I‐3 Hypervalent Iodine‐Based Compounds for Electrophilic Trifluoromethylation.

    Eisenberger P.; Gischig S.; Togni A. Chemistry – A European Journal 2006, 12 (9), 2579–2586. DOI: 10.1002/chem.200501052

  2. Trifluoromethyl-1,3-Dihydro-3,3-Dimethyl-1,2-Benziodoxole.

    Stanek K.; Koller R.; Kieltsch I.; Eisenberger P.; Togni A. Encyclopedia of Reagents for Organic Synthesis 2009. DOI: 10.1002/047084289X.rn01120

  3. Electrophilic Trifluoromethylation by Use of Hypervalent Iodine Reagents.

    Charpentier J.; Früh N.; Togni A. Chem Rev 2015, 115 (2), 650–682. DOI: 10.1021/cr500223h

 

 

 

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