390432-47-0Relevant academic research and scientific papers
Palladium-catalyzed aerobic oxidative coupling of allylic alcohols with anilines in the synthesis of nitrogen heterocycles
Kumar, Gangam Srikanth,Singh, Diksha,Kumar, Manish,Kapur, Manmohan
, p. 3941 - 3951 (2018/04/14)
We report herein an unprecedented and expedient Pd-catalyzed oxidative coupling of allyl alcohols with anilines to afford β-amino ketones which are converted into substituted quinolines in a one-pot fashion. The exclusive preference for N-alkylation over N-allylation makes this approach unique when compared to those reported in literature. Detailed mechanistic investigations reveal that the conjugate addition pathway was the predominant one over the allylic amination pathway. The notable aspects of the present approach are the use of readily available, bench-stable allyl alcohols and molecular oxygen as the terminal oxidant, in the process dispensing the need for unstable and costly enones. Further, we explored the synthetic utility of β-amino ketones through an intramolecular α-arylation methodology and a one-pot domino annulation, thereby providing rapid access to indolines and quinolines.
Intramolecular Pd-mediated processes of amino-tethered aryl halides and ketones: Insight into the ketone α-arylation and carbonyl-addition dichotomy. A new class of four-membered azapalladacycles
Sole, Daniel,Vallverdu, Lluis,Solans, Xavier,Font-Bardia, Merce,Bonjoch, Josep
, p. 1587 - 1594 (2007/10/03)
An exploration of the scope and limitations of Pd(O)-catalyzed intramolecular coupling reactions of amino-tethered aryl halides and ketones has been conducted. Two different and competitive reaction pathways starting from ω-(2-haloanilino) alkanones, enolate arylation and addition to the carbonyl group, have been observed, while ω-(2-halobenzylamino) alkanones exclusively underwent the enolate arylation process. The dichotomy between ketone α-arylation and carbonyl-addition in the reactions of ω-(2-haloanilino) alkanones has been rationalized by the intermediacy of unprecedented four-membered azapalladacycles, from which X-ray data and chemical behavior are reported.
