88675-40-5Relevant academic research and scientific papers
Palladium-catalyzed benzylic C(sp3)-H carbonylative arylation of azaarylmethyl amines with aryl bromides
Hu, Bowen,Walsh, Patrick J.,Xu, Lijin,Zhao, Haoqiang
, p. 10862 - 10870 (2021/08/25)
A highly selective palladium-catalyzed carbonylative arylation of weakly acidic benzylic C(sp3)-H bonds of azaarylmethylamines with aryl bromides under 1 atm of CO gas has been achieved. This work represents the first examples of use of such weakly acidic pronucleophiles in this class of transformations. In the presence of a NIXANTPHOS-based palladium catalyst, this one-pot cascade process allows a range of azaarylmethylamines containing pyridyl, quinolinyl and pyrimidyl moieties and acyclic and cyclic amines to undergo efficient reactions with aryl bromides and CO to provide α-amino aryl-azaarylmethyl ketones in moderate to high yields with a broad substrate scope and good tolerance of functional groups. This reaction proceeds via in situ reversible deprotonation of the benzylic C-H bonds to give the active carbanions, thereby avoiding prefunctionalized organometallic reagents and generation of additional waste. Importantly, the operational simplicity, scalability and diversity of the products highlight the potential applicability of this protocol.
Pd0-Catalyzed Four-Component Reaction of Aryl Halide, CO, N-Tosylhydrazone, and Amine
Liu, Yiyang,Zhang, Zhen,Zhang, Songnan,Zhang, Yan,Wang, Jianbo,Zhang, Zhenhua
supporting information, p. 3658 - 3663 (2018/10/31)
A Pd0-catalyzed four-component cascade reaction of an aryl halide, CO, an N-tosylhydrazone, and an amine affording α-amino ketone has been developed. This reaction involves a sequential carbonylation, metal carbene migratory insertion, and amination. Control experiments and DFT calculations further reveal the reaction sequence and chemoselectivity of individual components in this cascade process.
