Dicationic electrophiles from olefinic amines in superacid.

  title={Dicationic electrophiles from olefinic amines in superacid.},
  author={Yun Zhang and Aaron McElrea and Gregorio S{\'a}nchez and Dat Tien Do and Alma Gomez and Sharon L. Aguirre and Rendy Rendy and Douglas A. Klumpp},
  journal={The Journal of organic chemistry},
  volume={68 13},
This paper describes the superacid-catalyzed chemistry of olefinic amines and related compounds. A variety of olefinic amines are found to react with benzene in CF(3)SO(3)H (triflic acid) to give addition products in good yields (75-99%), including the pharmaceutical agents fenpiprane and prozapine. A general mechanism is proposed that invokes the formation of reactive, dicationic electrophiles and the direct observation of a diprotonated species is reported from low-temperature NMR experiments… 

Superacid-catalyzed reactions of olefinic pyrazines: an example of anti-Markovnikov addition involving superelectrophiles.

Olefinic pyrazines are found to react with benzene in CF3SO3H and give anti-Markovnikov-type addition products and it is suggested that acid-catalyzed addition reactions can giveAnti-MarkOVnikov- type products when a multiply charged group is adjacent to the olefinics site.

Superelectrophilic Activation of Phenylglyoxamides: Efficient Synthesis of Triarylacetamides and Fluorenecarboxamides by Superacid Catalysis

Direct synthesis of triarylacetamides and 9-fluorenecarboxamides has been achieved. Phenylglyoxamides upon superelectrophilic activation in trifluoromethanesulfonic acid (triflic acid, TFSA) leads to

Intramolecular Conjugate Additions with Heterocyclic Olefins.

In triflic acid-promoted reactions, conjugate addition is observed with pyrazine-, 2-pyrimidine-, and 2-quinoxaline-based olefins and a phenyl group nucleophile.

L-proline promoted Ullmann-type reaction of vinyl bromides with imidazoles in ionic liquids.

The Ullmann-type coupling reaction of vinyl bromides and imidazoles in ILs at 90-110 degrees C gave the corresponding N-vinylimidazoles in good to excellent yields by using L-proline as the ligand;

Ferric(III) Nitrate: An Efficient Catalyst for the Regioselective Friedel–Crafts Reactions of Indoles and tert-Enamides in Water

The ferric nitrate catalyzed Friedel–Crafts reactions of various indoles and tertiary enamides, which proceed in water at room temperature, are demonstrated for an efficient, atom-economical and

Phosphine-Catalyzed Aza-MBH Reactions of Vinylpyridines: Efficient and Rapid Access to 2,3,5-Triarylsubstituted 3-Pyrrolines.

Vinylpyridines have been developed in aza-Morita-Baylis-Hillman (MBH) reaction to construct triarylsubstituted 3-pyrrolines. The first electron-deficient aromatic ring is marked as an activating mode

Synthesis of diarylmethanes via metal-free reductive cross-coupling of diarylborinic acids with tosyl hydrazones.

This paper describes a practical and efficient procedure that takes advantage of diarylborinic acids as a cost-effective alternative to arylboronic acids for synthesis of diarylmethanes through


Dicationic electrophiles from olefinic amines in superacid.

  • 2003