27962-33-0Relevant academic research and scientific papers
Transition-metal-free C(sp3)-H/C(sp3)-H dehydrogenative coupling of saturated heterocycles with: N-benzyl imines
Deng, Guogang,Feng, Ping,Li, Minyan,Li, Tiantian,Liu, Zhengfen,Walsh, Patrick J.,Wei, Wanshi,Yang, Xiaodong,Zhang, Hongbin,Zi, Quanxing
, p. 7619 - 7625 (2020)
A unique C(sp3)-H/C(sp3)-H dehydrocoupling of N-benzylimines with saturated heterocycles is described. Using super electron donor (SED) 2-azaallyl anions and aryl iodides as electron acceptors, single-electron-transfer (SET) generates an aryl radical. Hydrogen atom transfer (HAT) from saturated heterocycles or toluenes to the aryl radical generates alkyl radicals or benzylic radicals, respectively. The newly formed alkyl radicals and benzylic radicals couple with the 2-azaallyl radicals with formation of new C-C bonds. Experimental evidence supports the key hydrogen-abstraction by the aryl radical, which determines the chemoselectivity of the radical-radical coupling reaction. It is noteworthy that this procedure avoids the use of traditional strong oxidants and transition metals. This journal is
Synthesis of (diarylmethyl)amines using Ni-catalyzed arylation of C(sp3)-H bonds
Fernández-Salas, José A.,Marelli, Enrico,Nolan, Steven P.
, p. 4973 - 4977 (2015)
The first nickel catalyzed deprotonative cross coupling between C(sp3)-H bonds and aryl chlorides is reported, allowing the challenging arylation of benzylimines in the absence of directing group or stoichiometric metal activation. This methodo
Synthesis of diarylmethylamines via palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions
Li, Minyan,Yuecel, Baris,Adrio, Javier,Bellomo, Ana,Walsh, Patrick J.
, p. 2383 - 2391 (2014/05/20)
Diarylmethylamines are of great interest due to their prevalence in pharmaceutical chemistry. As a result, new methods for their synthesis are in demand. Herein, we report a versatile protocol for the synthesis of diarylmethylamine derivatives involving palladium-catalyzed arylation of in situ generated 2-azaallyl anion intermediates. The 2-azaallyl anions are generated by reversible deprotonation of readily available aldimine and ketimine precursors. Importantly, the arylated aldimine and ketimine products do not undergo isomerization under the reaction conditions. Scale-up of the arylation and hydrolysis of the resulting products to furnish diarylmethylamines were also successfully performed. This journal is the Partner Organisations 2014.
Palladium-catalyzed decarboxylative benzylation of diphenylglycinate lmines
Fields, Wendy H.,Chruma, Jason J.
supporting information; experimental part, p. 316 - 319 (2010/03/24)
(Figure presented) General reaction conditions for the Pd-catalyzed decarboxylative benzylation of benzyl diphenylglycinate lmines are described. The overall procedure requires a simple catalyst/ligand combination to form a new Csp3-Csp3 bond. Microwave Irradiation greatly accelerated the transformation. Moreover, various heteroaromatlc moieties are tolerated in both the imine and ester components.
Efficient transamination under mild conditions: Preparation of primary amine derivatives from carbonyl compounds via imine isomerization with catalytic amounts of potassium tert-butoxide
Cainelli, Gianfranco,Giacomini, Daria,Trerè, Alessandra,Boyl, Pietro Pilo
, p. 5134 - 5139 (2007/10/03)
1,3-Prototropic rearrangement of N-diphenylmethanimines was successfully performed with a catalytic amount of potassium tert-butoxide. This procedure can also be used with aliphatic and aromatic aldimines and was extended to the isomerization of (1R)-camphorquinone monoimine and N-(4-methoxyphenyl)-4-phenyl-3-iminoazetidin-2-one. The isomerized imines were easily hydrolyzed and isolated as Cbz derivatives.
