4523-52-8Relevant articles and documents
Palladium-Catalyzed Highly Regioselective Aromatic Substitution of Benzylic Ammonium Salts with Amines
Xu, Ya-Nan,Zhu, Meng-Zeng,Lin, Yu-Kun,Tian, Shi-Kai
supporting information, p. 7169 - 7173 (2019/09/13)
An unprecedented aromatic substitution reaction of benzylic ammonium salts has been developed through palladium-catalyzed C-N bond cleavage. A range of primary and secondary amines participated in a palladium-catalyzed aromatic substitution reaction of benzylic ammonium salts, delivering sterically hindered aromatic amines in moderate to excellent yields with extremely high regioselectivity. Preliminary mechanistic studies permitted successful identification of Π-benzylpalladium complexes and Γ-vinyl allylic amines as key intermediates. This study paves the way for the use of benzylic ammonium salts in the aromatic substitution reactions.
Resonance-stabilized α-naphthylmethyl carbocations and spiro compounds based thereon: VII. Transformations of α-naphthylmethyl carbocations stabilized by one electron-donor group or peri-fused heteroring
Vinogradova,Filatova,Vistorobskii,Pozharskii,Borovlev,Starikova
, p. 338 - 348 (2007/10/03)
1-Hydroxymethyl- and 1-alkoxymethylnaphthalenes containing dimethylamino and methoxy groups or a heteroring in positions 4 and 5 react with protic and Lewis acids to give 1-naphthylmethyl carbocations. Reactions of the latter with the initial alcohol molecule lead to the formation of oligomerization or dehydrogenation (to aldehyde) products or the corresponding dinaphthylmethanes. In some cases, the process was accompanied by cyclodimerization to form cyclohexadienone spiro derivatives in a small yield. Pleiades Publishing, Inc., 2006.