36147-03-2Relevant articles and documents
Nickel-Catalyzed Formal Aminocarbonylation of Secondary Benzyl Chlorides with Isocyanides
Wang, Yun,Huang, Wenyi,Wang, Chenglong,Qu, Jingping,Chen, Yifeng
supporting information, p. 4245 - 4249 (2020/06/27)
Phenylacetamides represent versatile feedstocks in synthetic chemistry, widely existing in drug molecules and natural products. Herein, we disclose a nickel-catalyzed formal aminocarbonylation of secondary benzyl chlorides with isocyanides yielding α-substituted phenylacetamide with steric hindrance, which is synthetically challenging via palladium-catalyzed aminocarbonylation. The reaction features wide functional group tolerance under mild conditions, highlighted by the tolerance of various aromatic halide (-Cl, -Br, -I) and heteroaromatic rings (pyridine and pyrazine).
Experimental and Theoretical Study of the Reactivity of Primary and Secondary Enaminones toward Diphenylketene. A Comparison of AM1 and HAM/3 Semiempirical Methods
Eberlin, Marcos N.,Takahata, Yuji,Kascheres, Concetta
, p. 5150 - 5155 (2007/10/02)
Diazodiphenylethanone (1) reacts with acyclic enamino ketones 2 and enamino esters 3 to form products of electrophilic attack of diphenylketene at Cα (5) and nitrogen (6 and 7).The relative reactivity of the different enaminones was shown to be consistent with HOMO energies determined by the HAM/3 semiempirical method.However, this approach could not completely explain the reactivity of the cyclic enamino ketones 4, which, by HAM/3, show a high energy second HOMO corresponding to the nonbonded pair of electrons on oxygen.