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Electrophilic trifluoromethylation by use of hypervalent iodine reagents.
Charpentier J, Früh N, Togni A. Charpentier J, et al. Chem Rev. 2015 Jan 28;115(2):650-82. doi: 10.1021/cr500223h. Epub 2014 Aug 25. Chem Rev. 2015. PMID: 25152082 No abstract available.
Nickel(II)-catalyzed highly enantioselective hydrophosphination of methacrylonitrile.
Sadow AD, Haller I, Fadini L, Togni A. Sadow AD, et al. J Am Chem Soc. 2004 Nov 17;126(45):14704-5. doi: 10.1021/ja0449574. J Am Chem Soc. 2004. PMID: 15535679
A catalytic cycle involving 1,4-conjugate addition of R2PH to methacrylonitrile is supported by the isolation and characterization of a catalytically active N-coordinated, methacrylonitrile Ni complex....
A catalytic cycle involving 1,4-conjugate addition of R2PH to methacrylonitrile is supported by the isolation and characterization of
Enantioselective addition of secondary phosphines to methacrylonitrile: catalysis and mechanism.
Sadow AD, Togni A. Sadow AD, et al. J Am Chem Soc. 2005 Dec 7;127(48):17012-24. doi: 10.1021/ja0555163. J Am Chem Soc. 2005. PMID: 16316248
We propose a mechanism involving coordination of methacrylonitrile to the dicationic nickel catalyst followed by 1,4-addition of the phosphine, and then, rate-determining proton transfer. This mechanism is supported by (a) the experimentally determined rate law (rat …
We propose a mechanism involving coordination of methacrylonitrile to the dicationic nickel catalyst followed by 1,4-addition of the …
Novel 10-I-3 hypervalent iodine-based compounds for electrophilic trifluoromethylation.
Eisenberger P, Gischig S, Togni A. Eisenberger P, et al. Chemistry. 2006 Mar 8;12(9):2579-86. doi: 10.1002/chem.200501052. Chemistry. 2006. PMID: 16402401
The synthesis of a new family of 10-I-3 hypervalent iodine compounds is described in which the CF3 functionality participates directly in the hypervalent bond. ...The overall process can be understood as a formal umpolung of the CF3 group....
The synthesis of a new family of 10-I-3 hypervalent iodine compounds is described in which the CF3 functionality participates directl …
Mild electrophilic trifluoromethylation of secondary and primary aryl- and alkylphosphines using hypervalent iodine(iii)-CF(3) reagents.
Eisenberger P, Kieltsch I, Armanino N, Togni A. Eisenberger P, et al. Chem Commun (Camb). 2008 Apr 7;(13):1575-7. doi: 10.1039/b801424h. Epub 2008 Mar 3. Chem Commun (Camb). 2008. PMID: 18354804
A direct, mild and efficient trifluoromethylation of primary and secondary phosphines is achieved with easily accessible, cheap hypervalent iodine compounds acting as electrophilic CF(3)-transfer reagents....
A direct, mild and efficient trifluoromethylation of primary and secondary phosphines is achieved with easily accessible, cheap hyper
Reactivity of a 10-I-3 hypervalent iodine trifluoromethylation reagent with phenols.
Stanek K, Koller R, Togni A. Stanek K, et al. J Org Chem. 2008 Oct 3;73(19):7678-85. doi: 10.1021/jo8014825. Epub 2008 Sep 5. J Org Chem. 2008. PMID: 18771328
The reaction of the 10-I-3 hypervalent iodine electrophilic trifluoromethylation reagent 1-trifluoromethyl-1,2-benziodoxol-3-(1H)-one (2) with 2,4,6-trimethylphenol, after deprotonation with NaH and in the presence of 18-crown-6 in a polar, nonprotic solvent, affords 1,3,5 …
The reaction of the 10-I-3 hypervalent iodine electrophilic trifluoromethylation reagent 1-trifluoromethyl-1,2-benziodoxol-3-(1H)-one (2) wi …
Ni(II)-catalyzed enantioselective Nazarov cyclizations.
Walz I, Togni A. Walz I, et al. Chem Commun (Camb). 2008 Sep 28;(36):4315-7. doi: 10.1039/b806870d. Epub 2008 Jul 17. Chem Commun (Camb). 2008. PMID: 18802555
Nazarov cyclizations are catalyzed by a dicationic Ni(II) complex containing the chiral tridentate phosphine Pigiphos; the catalyst exerts a high degree of torquoselectivity and affords the products in up to 88% ee....
Nazarov cyclizations are catalyzed by a dicationic Ni(II) complex containing the chiral tridentate phosphine Pigiphos; the catalyst e …
Zinc-mediated formation of trifluoromethyl ethers from alcohols and hypervalent iodine trifluoromethylation reagents.
Koller R, Stanek K, Stolz D, Aardoom R, Niedermann K, Togni A. Koller R, et al. Angew Chem Int Ed Engl. 2009;48(24):4332-6. doi: 10.1002/anie.200900974. Angew Chem Int Ed Engl. 2009. PMID: 19434641
A (fluor)ry of activity: The transfer of an intact trifluoromethyl group from a hypervalent iodine reagent to an aliphatic alcohol occurs smoothly upon activation by zinc bis(triflimide). This constitutes a straightforward method for the preparation of triflu
A (fluor)ry of activity: The transfer of an intact trifluoromethyl group from a hypervalent iodine reagent to an aliphatic alc
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