66757-87-7Relevant articles and documents
Deconstructive di-functionalization of unstrained, benzo cyclic amines by C-N bond cleavage using a recyclable tungsten catalyst
Zhang, Yujing,Sun, Shuai,Su, Yijin,Zhao, Jian,Li, Yong-Hong,Han, Bo,Shi, Feng
supporting information, p. 4970 - 4974 (2019/05/29)
With H2WO4 as the catalyst and H2O2 as the oxidant, we herein report a deconstructive difunctionalization of the C-N bond in unstrained, benzo cyclic amines to generate an ester group and nitro group simultaneously. The preliminary mechanistic studies suggested that the corresponding hydroxamic acid is the key intermediate for this transformation. Importantly, with the utilization of this transformation, we achieved an interesting approach for the ring contraction of quinoline to indole, an example of scaffold hopping in a hetero-aromatic system.
Base directed palladium catalysed Heck arylation of acrolein diethyl acetal in water
Al-Maksoud, Walid,Menuel, Stéphane,Jahjah, Mohamad,Monflier, Eric,Pinel, Catherine,Djakovitch, Laurent
, p. 250 - 258 (2013/11/19)
The selective Heck arylation of acrolein diethyl acetal catalysed by [Pd(NH3)4]Cl2 in the presence of RAME-β-CD in water as solvent is described. Depending on the base (i.e. NaOAc or HN(i-Pr)2) good to high selectivity's towards, respectively, the cinnamaldehydes 2 or the 3-arylpropionic esters 1 were achieved. The results support that depending on the base different palladium intermediate complexes are formed. Using NaOAc, {[ArPdX(H2O)2]} complex is preferentially generated giving the cinnamaldehyde 2. On the other hand, in the presence of HN(i-Pr)2, a L-type ligand, [ArPdX(HN(i-Pr) 2(H2O)] or [ArPdX(HN(i-Pr)2(HN(i-Pr) 2)] will be generated leading to the formation of the 3-arylpropionic ester 1. For the last, coordinated amine participates very probably to the formation of the esters through intramolecular syn β-H elimination.
Original TDAE strategy using α-halocarbonyl derivatives
Since, Marc,Terme, Thierry,Vanelle, Patrice
experimental part, p. 6128 - 6134 (2011/03/19)
We report herein the selective C-C bond formation by the reaction of nitrobenzyl carbanions, formed via the TDAE strategy, with α-haloesters and α-haloamides. This reaction, extended in benzodioxole and dimethoxybenzene series provides new potentially CNS