1273223-84-9Relevant academic research and scientific papers
Vinylcyclopropanes as All-Carbon 1,5-Dipoles: A Reactivity Switch for Palladium-Catalyzed (5 + 4) Cycloadditions
Scuiller, Ana?s,Karnat, Alexandre,Casaretto, Nicolas,Archambeau, Alexis
, p. 2332 - 2336 (2021)
Azonanes were prepared by a palladium-catalyzed (5 + 4) cycloaddition between activated vinylcyclopropanes and 1-azadienes. During this process, the vinylcyclopropane partner displayed an unusual reactivity and behaved as an all-carbon 1,5-dipole. A N,N-bidentate ligand was required to inhibit the formation of thermodynamic (3 + 2) cycloadducts.
A Palladium-Catalyzed Oxa-(4+4)-Cycloaddition Strategy towards Oxazocine Scaffolds
Scuiller, Ana?s,Liu, Xueyang,Cordier, Marie,Garrec, Julian,Archambeau, Alexis
supporting information, p. 981 - 986 (2021/06/02)
A Pd-catalyzed oxa-(4+4)-cycloaddition between 1-azadienes and (2-hydroxymethyl)allyl carbonates is described. Aurone-derived azadienes furnished polycyclic 1,5-oxazocines in good yields. Interestingly, linear azadienes have also been involved and yielded monocyclic heterocycles with complete regioselectivity. DFT calculations were carried out to gain insight on this observation.
Rhodium-Catalyzed Annulative Coupling of Isothiazoles with Alkynes through N-S Bond Cleavage
Mihara, Gen,Noguchi, Teppei,Nishii, Yuji,Hayashi, Yoshihiro,Kawauchi, Susumu,Miura, Masahiro
supporting information, p. 661 - 665 (2020/01/31)
A Rh(III)-catalyzed annulative coupling of 3,5-diarylisothiazoles and alkynes is reported. The N-S bond in the isothiazole ring acts as an internal oxidant to regenerate the Rh(III) species in combination with an external Cu(II) oxidant, and the corresponding 1:2 coupling products are obtained. The remarkable difference in the reaction outcome between isothiazoles and the relevant isoxazoles has been investigated by DFT calculations, revealing that the relative stability of the enolate intermediates dictates the product selectivity.
