54521-26-5Relevant academic research and scientific papers
Reinvestigation of aminomethyltrifluoroborates and their application in suzuki-miyaura cross-coupling reactions
Raushel, Jessica,Sandrock, Deidre L.,Josyula, Kanth V.,Pakyz, Deborah,Molander, Gary A.
experimental part, p. 2762 - 2769 (2011/06/17)
A reinvestigation into the chemical composition of potassium aminomethyltrifluoroborates is reported. These trifluoroborato salts have been reassigned as zwitterionic ammoniomethyltrifluoroborates. Minor adjustments to the previously disclosed reaction conditions are reported that permit a similar level of activity as nucleophiles in Suzuki-Miyaura cross-coupling reactions.
Cross-coupling of mesylated phenol derivatives with potassium ammonio-and amidomethyltrifluoroborates
Molander, Gary A.,Beaumard, Floriane
supporting information; experimental part, p. 1242 - 1245 (2011/05/03)
A large array of aryl and heteroaryl mesylates have been successfully employed as electrophiles in a Csp2-Csp3 Suzuki-Miyaura cross-coupling with potassium ammonio-and amidomethyltrifluoroborates to afford the corresponding products
Base catalyzed intramolecular cyclization of dialkycrotyl(3-alkenylpropyn- 2-yl)ammonium salts and aqueous base fission of 2,2-dialkyl-4-methyl-and 2,2-dialkyl-4,6-dimethyl-2,6,7,7a-tetrahydro-1H-isoindolium bromides
Chukhajian,Nalbandyan,Gevorkyan,Shakhatuni,Panosyan
experimental part, p. 671 - 676 (2009/04/06)
Cyclization of dimethylcrotyl(3-vinyl-or-3-isopropenylpropyn-2-yl)ammonium bromides in the presence of base gave a mixture of the isomeric 2,2-dialkyl-4-methyl-and 2,2-dialkyl-4,6-dimethyl-2,6,7,7a-tetrahydro-1H- isoindolium bromides. Basic fission of the salts obtained at increased temperature gave a mixture of the isomeric N,N-disubstituted di-and trimethylbenzylamines whose structures were confirmed by their IR, 1H NMR, and 13C NMR spectra.
Scope of aminomethylations via Suzuki-Miyaura cross-coupling of orsanotrifluoroborates
Molander, Gary A.,Gormisky, Paul E.,Sandrock, Deidre L.
, p. 2052 - 2057 (2008/09/19)
(Chemical Equation Presented) We previously reported the Suzuki-Miyaura reaction of N,N-dialkylaminomethyltrifluoroborates with aryl bromides. Herein, we report a further investigation of the scope and limitations of this palladium-catalyzed aminomethylation reaction. Aryl chlorides, iodides, and triflates coupled in good to excellent yields to give N,N-dialkylbenzylic amines. The aminomethylation of alkenyl bromides was also examined.
