1287287-06-2Relevant academic research and scientific papers
CuI-catalyzed N,N’-diarylation of diamines of adamantane series
Panchenko,Abel,Averin,Maloshitskaya,Savelyev,Orlinson,Novakov,Beletskaya
, p. 1550 - 1555 (2017/03/01)
A copper(I) complex-catalyzed N,N’-diarylation of diamines based on 1,3-disubstituted adamantane, using aryl iodides bearing electron-donating and electron-withdrawing substituents, was studied. In the case of 2,2’-(adamantane-1,3-diyl)ethanediamine, the optimal catalyst system is CuI—2-(isobutyryl)cyclohexanone—Cs2CO3—DMF. The highest yield of diarylation product was reached in the case of 4-methoxyiodobenzene (79%). In the case of more spatially hindered adamantane-1,3-diyldimethanamine, 1,1’-binaphthalene-2,2’-diol (BINOL) should be used, with the highest yield of the target product (84%) being reached in the reaction with iodobenzene.
Arylation of adamantanamines: III.* Palladium-catalyzed arylation of adamantane-1,3-diyldimethanamine and 2,2′-(adamantane-1,3-diyl) diethanamine
Averin,Ulanovskaya,Buryak,Savel'ev,Orlinson,Novakov,Beletskaya
experimental part, p. 30 - 40 (2011/04/26)
Palladium-catalyzed arylation of adamantane-1,3-diyldimethanamine and 2,2′-(adamantane-1,3-diyl) diethanamine with isomeric bromochloro- and dibromobenzenes was studied. The yields of N,N′-diarylation products depend on the initial diamine and dihalobenzene structure. Side reactions were revealed, which reduced the yield of the target products. The arylation of 2,2′-(adamantane-1,3-diyl)diethanamine gives the corresponding N,N′-diaryl derivatives with better yield. The possibility for synthesizing unsymmetrical N,N′-diaryl derivatives of 2,2′- (adamantane-1,3-diyl)diethanamine was demonstrated.
