1561041-95-9Relevant academic research and scientific papers
Palladium-Catalyzed γ,γ′-Diarylation of Free Alkenyl Amines
Fu, Yu,Grant, Aaron J.,Landge, Vinod G.,Payton, John L.,Rabon, Allison M.,Young, Michael C.
, p. 10352 - 10360 (2021/07/26)
The direct difunctionalization of alkenes is an effective way to construct multiple C-C bonds in one-pot using a single functional group. The regioselective dicarbofunctionalization of alkenes is therefore an important area of research to rapidly obtain complex organic molecules. Herein, we report a palladium-catalyzed γ,γ′-diarylation of free alkenyl amines through interrupted chain walking for the synthesis of Z-selective alkenyl amines. Notably, while 1,3-dicarbofunctionalization of allyl groups is well precedented, the present disclosure allows 1,3-dicarbofunctionalization of highly substituted allylamines to give highly Z-selective trisubsubstituted olefin products. This cascade reaction operates via an unprotected amine-directed Mizoroki-Heck (MH) pathway featuring a β-hydride elimination to selectively chain walk to furnish a new terminal olefin which then generates the cis-selective alkenyl amines around the sterically crowded allyl moiety. This operationally simple protocol is applicable to a variety of cyclic, branched, and linear secondary and tertiary alkenylamines, and has a broad substrate scope with regard to the arene coupling partner as well. Mechanistic studies have been performed to help elucidate the mechanism, including the presence of a likely unproductive side C-H activation pathway.
Gold(i)-catalysed [1,3] O→C rearrangement of allenyl ethers
Kona, Chandrababu Naidu,Ramana, Chepuri V.
supporting information, p. 2152 - 2154 (2014/02/14)
A simple and rapid access to the α-substituted acryl aldehydes has been provided by developing a gold-catalysed [1,3] rearrangement of the allenyl ethers importantly with a record turnover frequency of 4600 h-1 (at 0.05 mol% of the catalyst concentration) in homogeneous gold(i) catalysis. The Royal Society of Chemistry.
