1337984-75-4Relevant academic research and scientific papers
Copper-Catalyzed Cross-Dehydrogenative Coupling of N-Iminoquinolinium Ylides with Secondary Amines
Hua, Zerui,Fang, Lei,Wu, Shengying,Wang, Limin
, p. 4953 - 4956 (2016)
The copper-catalyzed cross-dehydrogenative coupling of N-iminoquinolinium ylides with secondary amines led to ortho-amino-substituted quinoline derivatives with high levels of regioselectivity in good yields. This direct C–H bond amination transformation employs CuI as the catalyst without the use of a ligand, external oxidant, or base. The reaction is operationally simple and can be conducted under mild conditions. The N-benzoyl directing group can be removed without any additional steps.
Synthesis of 2- and 2,3-substituted Pyrazolo[1,5- a ]pyridines: Scope and mechanistic considerations of a domino direct alkynylation and cyclization of n -iminopyridinium ylides using alkenyl bromides, alkenyl iodides, and alkynes
Mousseau, James J.,Bull, James A.,Ladd, Carolyn L.,Fortier, Angelique,Sustac Roman, Daniela,Charette, Andre B.
experimental part, p. 8243 - 8261 (2012/01/03)
Direct functionalization and tandem processes have both received considerable recent interest due to their cost and time efficiency. Herein we report the synthesis of difficult to obtain 2-substituted pyrazolo[1,5-a] pyridines through a tandem palladium-catalyzed/silver-mediated elimination/direct functionalization/cyclization reaction involving N-benzoyliminopyridinium ylides. As such, these biologically important molecules are prepared in an efficient, high-yielding manner, only requiring a two-step sequence from pyridine. Aryl-substituted alkenyl bromides and iodides are effective ylide coupling partners. Mechanistic studies led to the use of terminal alkynes, which extended the scope of the reaction to include alkyl substitution on the unsaturated reactive site. The optimization, scope, and mechanistic considerations of the process are discussed.
