107261-83-6Relevant academic research and scientific papers
Direct use of allylic alcohols for platinum-catalyzed monoallylation of amines
Utsunomiya, Masaru,Miyamoto, Yoshiki,Lpposhi, Junji,Ohshima, Takashi,Mashima, Kazushi
, p. 3371 - 3374 (2007)
A new direct catalytic amination of allylic alcohols promoted by the combination of platinum and a large bite-angle ligand DPEphos was developed in which the allylic alcohol was effectively converted to a π-allylplatinum intermediate without the use of an activating reagent. The use of the DPEphos ligand was essential for obtaining high catalyst activity and high monoallylation selectivity of primary amines, allowing the formation of a variety of monoallylation products in good to excellent yield.
Allylic Amination of Alkenes with Iminothianthrenes to Afford Alkyl Allylamines
Chen, Junting,Cheng, Qiang,Lin, Songyun,Ritter, Tobias
, p. 17287 - 17293 (2020/11/02)
Allylic C-H amination is currently accomplished with (sulfon)amides or carbamates. Here we show the first allylic amination that can directly afford alkyl allylamines, enabled by the reactivity of thianthrene-based nitrogen sources that can be prepared from primary amines in a single step.
Facile synthesis of Z -alkenes via uphill catalysis
Singh, Kamaljeet,Staig, Shannon J.,Weaver, Jimmie D.
supporting information, p. 5275 - 5278 (2014/05/06)
Catalytic access to thermodynamically less stable Z-alkenes has recently received considerable attention. These approaches have relied upon kinetic control of the reaction to arrive at the thermodynamically less stable geometrical isomer. Herein, we present an orthogonal approach which proceeds via photochemically catalyzed isomerization of the thermodynamic E-alkene to the less stable Z-isomer which occurs via a photochemical pumping mechanism. We consider two potential mechanisms. Importantly, the reaction conditions are mild, tolerant, and operationally simple and will be easily implemented.
An efficient and convenient palladium catalyst system for the synthesis of amines from allylic alcohols
Banerjee, Debasis,Jagadeesh, Rajenahally V.,Junge, Kathrin,Junge, Henrik,Beller, Matthias
, p. 2039 - 2044 (2013/01/15)
A novel catalyst system for efficient amination of allylic alcohols with aryl and alkyl amines is presented. By applying a convenient combination consisting of Pd(OAc)2/1,10-phenanthroline, a variety of allylic alcohols reacted smoothly to give the corresponding secondary and tertiary amines in good to excellent yields with high regioselectivity. The usefulness of our protocol is demonstrated in the one-step synthesis of the antifungal drug naftifine and the calcium channel blocker flunarizine. One pot is all it takes: By applying a convenient combination consisting of Pd(OAc)2/1,10- phenanthroline, a variety of allylic alcohols reacts smoothly to give the corresponding secondary and tertiary amines in good to excellent yields with high regioselectivity (see picture).
Palladium-tetraphosphine catalysed allylic substitution in water
Feuerstein, Marie,Laurenti, Dorothée,Doucet, Henri,Santelli, Maurice
, p. 2313 - 2315 (2007/10/03)
The cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane/[PdCl (C3H5)]2 system catalyses allylic amination in water with very high substrate/catalyst ratio in good yields. A turnover number of 980 000 can be obtained for the addition of dipropylamine to allyl acetate in the presence of this catalyst.
