21865-49-6Relevant academic research and scientific papers
Scalable and safe synthetic organic electroreduction inspired by Li-ion battery chemistry
Peters, Byron K.,Rodriguez, Kevin X.,Reisberg, Solomon H.,Beil, Sebastian B.,Kawamata, Yu,Baran, Phil S.,Hickey, David P.,Klunder, Kevin,Gorey, Timothy J.,Anderson, Scott L.,Minteer, Shelley D.,Collins, Michael,Starr, Jeremy,Chen, Longrui,Udyavara, Sagar,Neurock, Matthew
, p. 838 - 845 (2019/04/30)
Reductive electrosynthesis has faced long-standing challenges in applications to complex organic substrates at scale. Here, we show how decades of research in lithium-ion battery materials, electrolytes, and additives can serve as an inspiration for achieving practically scalable reductive electrosynthetic conditions for the Birch reduction. Specifically, we demonstrate that using a sacrificial anode material (magnesium or aluminum), combined with a cheap, nontoxic, and water-soluble proton source (dimethylurea), and an overcharge protectant inspired by battery technology [tris(pyrrolidino)phosphoramide] can allow for multigram-scale synthesis of pharmaceutically relevant building blocks. We show how these conditions have a very high level of functional-group tolerance relative to classical electrochemical and chemical dissolving-metal reductions. Finally, we demonstrate that the same electrochemical conditions can be applied to other dissolving metal-type reductive transformations, including McMurry couplings, reductive ketone deoxygenations, and epoxide openings.
Gold(I)-catalysed cascade reactions in the synthesis of 2,3-fused indole derivatives
Gimeno, Ana,Rodríguez-Gimeno, Alejandra,Cuenca, Ana B.,Ramírez De Arellano, Carmen,Medio-Simón, Mercedes,Asensio, Gregorio
supporting information, p. 12384 - 12387 (2015/08/03)
A gold(I)-catalysed hydroaminative/arylative cascade for the efficient synthesis of a variety of indole-fused skeletons has been developed. Factors controlling the catalyst loading required in these transformations involving 1,3-unsubstituted indole intermediates have been revealed, allowing isolation of an unprecedented 1,3-dimetallated 3H-indole gold complex characterized by X-ray diffraction.
Comportement cathodique compare du carbazole, du dibenzothiophene et du dibenzofuranne: coupure ou hydrogenation
Belkasmioui, Ahmed,Simonet, Jacques
, p. 699 - 702 (2007/10/02)
Title heterocycles are cathodically reduced in weakly protic media.Under such conditions N-substituted carbazoles, dibenzothiophene and dibenzofuran lead selectively to 1,4-dihydro forms.The cleavage of carbon-heteroatom bonds is never observed.
