1091-93-6Relevant articles and documents
Birch Reductions of Methoxyaromatics in Aqueous Solution
Swenson, Karl E.,Zemach, Dvora,Nanjundiah, Chenniah,Kariv-Miller, Essie
, p. 1777 - 1779 (1983)
A Birch-like electroreduction of methoxyaromatics in aqueous solutions was achieved, probably through the intermediacy of a tetrabutylammonium amalgam.
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.
The synthesis and evaluation of functionalized estratropones: Potent inhibitors of tubulin polymerization
Miller, Thomas A.,Bulman, Amanda L.,Thompson, Charles D.,Garst, Michael E.,Macdonald, Timothy L.
, p. 1851 - 1856 (2007/10/03)
The synthesis of several ex-substituted estratropones is described. The compounds were evaluated for the inhibition of tubulin polymerization using purified bovine brain tubulin. Several of the compounds are equipotent to colchicine for their ability to inhibit the polymerization of tubulin.
