1240949-70-5Relevant academic research and scientific papers
Pyrrole as a Directing Group: Regioselective Pd(II)-Catalyzed Alkylation and Benzylation at the Benzene Core of 2-Phenylpyrroles
Wiest, Johannes M.,P?thig, Alexander,Bach, Thorsten
, p. 852 - 855 (2016)
Pyrrole has been employed for the first time as a directing group in the Pd(II)-catalyzed ortho-functionalization of C(sp2)-H bonds. A variety of substituted 2-phenylpyrroles were successfully methylated, alkylated, or benzylated in the ortho-position of the benzene ring, yielding the respective 2-substituted pyrrol-2-yl benzenes (36 examples, 51-93% yield). Neither additives nor additional ligands were required to perform the reaction, which was routinely conducted with PdBr2 as the catalyst and Li2CO3 as the base. Mechanistically, there is evidence that precoordination of palladium to the pyrrole enables the regioselective ortho-attack. (Chemical Equation Presented).
One-Step, Effective, and Cascade Syntheses of Highly Functionalized Cyclopentenes with High Diastereoselectivity
Alishetty, Suman,Shih, Hong-Pin,Han, Chien-Chung
supporting information, p. 2513 - 2516 (2018/05/17)
Tetrabutylammonium fluoride works as an effective organocatalyst for the cycloaddition between phenacylmalononitriles and electron-deficient olefins (having substituent groups of NO2, CHO, and COR), providing a facile synthetic route to versatile multifunctionalized cyclopentenes having an allylic quaternary carbon center bearing both cyano and carboxamide groups with high yields and high diastereoselectivity. Preliminary studies reveal that these functionalized cyclopentenes are convenient precursors for making α-cyano-functionalized cyclopentadienone oximes.
