Indium-Mediated Deoxygenation of Nitrones, N-Oxides and Deoxygenative Reductive Coupling of Nitrones to Vicinal Diamines

Simple electrochemical reduction of nitrones to amines

“…In fact, the reduction of open nitrones to amines needs two independent steps or at least two different reagents for both reductions 4. The first step, which allows the formation of the imine through a deoxygenation process, is normally performed using a metal,4,5 even though there are also examples using different organic reagents 6. However, many of these methods are limited by harsh procedures, side reactions or lack of chemoselectivity, whereas the second one to yield the final amine has been often carried out through hydrogenation or the use of hydrides 7.…”

Samarium Diiodide-Induced Reductive Cross-Coupling of Nitrones with Aldehydes and Ketones

“…[1] They have also been used as in vivo protective agents against radicals generated by oxidative stress. [2] Surprisingly, nitrones have seldom been involved in radical reactions aimed to create C À C bonds, [3,4] even though the addition of radicals to other CN bonds is known. [5] We decided to explore the possibility of reductive cross-coupling between nitrones and carbonyl compounds, promoted by samarium diiodide, to produce vicinal amino alcohols.…”

Remarkably Efficient Synthesis of 2H-Indazole 1-Oxides and 2H-Indazoles via Tandem Carbon−Carbon Followed by Nitrogen−Nitrogen Bond Formation

“…Attempts to deoxygenate the resin-bound indazole oxides using InCl 3 54,55 was not successful, overnight reaction at elevated temperature (100 °C) yielded indazoles only in single-digit percentage points. Reduction with SmI 2 yielded a mixture of products.…”