Togni reagent II

CAS 887144-94-7, Cat. No EN300-136055
Reagent for the nucleophilic introduction of trifluoromethyl groups

Togni Reagent II

Togni reagent II is a highly effective electrophilic trifluoromethylating reagent. The reagent is a colorless, crystalline solid that soluble in polar organic solvents. It offers trifluoromethylation of carbon- and sulfur-centered nucleophiles, copper-catalyzed trifluoromethylation of unactivated olefins, trifluoromethylation of phenol derivatives, zinc-mediated formation of trifluoromethyl ethers from alcohols[1], [2]. Togni reagent II has a predictable positional selectivity and a high level of functional group compatibility[3]. But despite simple procedures and mild reaction conditions, the reagent has explosive properties that are important to remember when working with it[4], [5].

Synonyms: 1-(Trifluoromethyl)-1,2-benziodoxol-3(1H)-one, 1-Trifluoromethyl-1,2-benziodoxol-3(1H)-one, 1-Trifluoromethyl-1,2-benziodoxol-3-(1H)-one

Selected publication

  1. Copper‐Catalyzed Trifluoromethylation of Unactivated Olefins.

    Parsons A. T.; Buchwald S. L. Angewandte Chemie International Edition 2011, 50 (39), 9120–9123. DOI: 10.1002/anie.201104053

  2. Mild Electrophilic Trifluoromethylation of Carbon‐ and Sulfur‐Centered Nucleophiles by a Hypervalent Iodine(III)–CF3 Reagent.

    Kieltsch I.; Eisenberger P.; Togni A. Angewandte Chemie International Edition 2007, 46 (5), 754–757. DOI: 10.1002/anie.200603497

  3. 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

  4. Notification about the Explosive Properties of Togni’s Reagent II and One of Its Precursors.

    Fiederling N.; Haller J.; Schramm H. Org Process Res Dev 2013, 17 (3), 318–319. DOI: 10.1021/op400035b

  5. 2,2,2-Trifluoroethyl Formate.

    Smith C. R. Encyclopedia of Reagents for Organic Synthesis 2010. DOI: 10.1002/047084289X.rn01159