32578-29-3Relevant academic research and scientific papers
Preparation and Palladium-Catalyzed Cross-Coupling of Aryl Triethylammonium Bis(catechol) Silicates with Aryl Triflates
Seganish, W. Michael,DeShong, Philip
, p. 1137 - 1143 (2007/10/03)
Pentavalent aryl and heteroaryl bis(catechol) silicates undergo palladium-catalyzed cross-coupling with aryl and heteroaryl triflates in the presence of a fluoride source in excellent yields. These solid, air-stable bis(catechol) silicates are prepared from a high-yielding displacement reaction between catechol and an aryl siloxane in the presence of an amine base. The cross-coupling reaction is tolerant of a wide range of electron-donating and electron-withdrawing groups. Several examples of di-ortho-substituted triflates are successfully coupled with these reagents.
Potassium organotrifluoroborates: New partners in palladium-catalysed cross-coupling reactions
Darses, Sylvain,Michaud, Guillaume,Genet, Jean-Pierre
, p. 1875 - 1883 (2007/10/03)
The preparation of various potassium organotrifluoroborates bearing either aryl, alkenyl, or alkynyl substituents is described. These stable salts are shown to be very efficient partners in palladium-catalysed cross- coupling reactions with arenediazonium salts, affording biaryl and styrene derivatives in high yields.
Oxidation Reduction Reactions Involving Nitro Groups in Trifluoromethanesulfonic Acid. Part 2. The Reactions of Chloromethylbenzenes with Aromatic Nitro Compounds
Austin, Rupert P.,Ridd, John H.
, p. 1205 - 1210 (2007/10/02)
2-Chloro-1,3-dimethylbenzene reacts with 1,4-dinitrobenzene in trifluoromethanesulfonic acid (99percent) at 70 deg C to give, after quenching, a 45percent yield of tris(4-chloro-3,5-dimethylphenyl)methanol.Some other chloro compounds and a range of aromat
Oxidation-Reduction Reactions Involving Nitro Groups in Trifluoromethanesulfonic Acid. Part 3. The Reactions of 2-Nitrobenzyl Alcohol and Related Compounds
Austin, Rupert P.,Ridd, John H.
, p. 1411 - 1414 (2007/10/02)
2-Nitrobenzyl alcohol reacts with trifluoromethanesulfonic acid (99percent) at 90 deg C to give a 66percent yield of 4-amino-3-carboxyphenyl trifluoromethanesulfonate 4.The reaction occurs through the intermediate formation of the C-protonated conjugate acid of anthranil N-oxide 7 and then probably involves the mono- and di-protonated forms of 2-nitrosobenzaldehyde.Under the same conditions, 2-nitrobenzyl chloride and 2-nitrosobenzaldehyde react to give the same product in essentially the same yield.Low temperature reactions in trifluoromethanesulfonic acid permit the conversion of N-phenylhydroxylamine into 4-aminophenyl trifluoromethanesulfonate in a yield of 78percent.
N- and C-Attacks of Phenylnitrenium Ions Generated from Phenyl Azides in the Presence of Trifluoroacetic Acid and/or Trifluoromethanesulphonic Acid
Takeuchi, Hiroshi,Takano, Katsuyuki
, p. 611 - 618 (2007/10/02)
Phenylnitrenium ions were generated from phenyl azides in the presence of trifluoroacetic acid (TFA) and/or trifluoromethanesulphonic acid (TFSA).Unsubstituted phenylnitrenium ions and those with an electron-withdrawing group such as NO2 or CN undergo aromatic N-substitution, whereas those with an electron-donating group such as Me, OMe, CH2Ph, or Ph undergo C-substitution, hydrogen abstraction, and tar formation.The special character of TFA and TFSA as compared with other acids is discussed.
