132982-92-4Relevant academic research and scientific papers
Arylation of adamantanamines: V. Palladium-catalyzed amination of isomeric chloroquinolines with diamines of the adamantane series
Grigorova,Averin,Abel,Maloshitskaya,Butov,Savelyev,Orlinson,Novakov,Beletskaya
, (2012)
Palladium-catalyzed arylation of diamines of the adamantane series with isomeric 2-, 4-, and 6-chloroquinoline was studied, and optimal conditions for the synthesis of the corresponding N,N′-diaryl derivatives were found. N,N-Diarylation products of prima
Nickel-Catalyzed Photoredox-Mediated Cross-Coupling of Aryl Electrophiles and Aryl Azides
Konev, Mikhail O.,McTeague, T. Andrew,Johannes, Jeffrey W.
, p. 9120 - 9124 (2018/09/25)
Medicinally relevant diarylamines are prepared through a photoredox-mediated dual catalytic nickel/ruthenium system from aryl azides and aryl electrophiles. Photoreduction of the aryl azide is proposed to proceed through an arylnickel-azide complex, which upon reduction and loss of nitrogen, generates a nickel(III) species capable of facile reductive elimination to afford the desired C-N bond formation. A variety of functionalized (hetero)aryl electrophiles are shown to participate in the coupling, including iodides, bromides, chlorides, and triflates. The reactions are simple to set up and are performed under ambient conditions, without the exclusion of oxygen or moisture.
Palladium-catalyzed amination of aryl and heteroaryl tosylates at room temperature
Ogata, Tokutaro,Hartwig, John F.
supporting information; experimental part, p. 13848 - 13849 (2009/02/07)
Mild palladium-catalyzed aminations of aryl tosylates and the first aminations of heteroaryl tosylates are described. In the presence of the combination of L2Pd(0) (L = P(o-tol)3) and the hindered Josiphos ligand CyPF-t-Bu, a variety of primary alkylamines and arylamines react with both aryl and heteroaryl tosylates at room temperature to form the corresponding secondary arylamines in high yields with complete selectivity for the monoarylamine. These reactions at room temperature occur in many cases with catalyst loadings of 0.1 mol % and 0.01 mol % in one case, constituting the most efficient aminations of aryl tosylates by nearly 2 orders of magnitude. This catalyst is made practical by the development of a convenient method to synthesize the L2Pd(0) precursor. This complex is stable to air as a solid. In contrast to conventional relative rates for reactions of aryl sulfonates, the reactions of aryl tosylates are faster than parallel reactions of aryl triflates, and the reactions of aryl tosylates are faster than parallel or competitive reactions of aryl chlorides. Copyright
