Nitroalkenes as Amination Tools

Iron-Mediated Radical Halo-Nitration of Alkenes

“…Finally, one-pot synthesis of useful nitroalkenes using this iron-mediated nitration reaction was examined . After decene ( 3a ) had been treated with Fe(NO 3 ) 3 ·9H 2 O/FeCl 3 in boiling MeCN, addition of Et 3 N to the reaction mixture afforded a complex mixture (Table , entry 1).…”

Applications of CeCl3 as an Environmental Friendly Promoter in Organic Chemistry

“…22c It is known that nitroalkenes are one of the strongest Michael acceptors, 386 providing a common pathway to nitroalkanes, 387 which could serve as stock compounds for corresponding amino compounds. 388 The reaction pro-ceeds with good yields even in the case of poorly reactive indoles, 389 and the corresponding adduct is in satisfactory yield obtained in the case of an indole derivative containing a hydroxyl group. Direct reaction of hydroxylindoles is generally problematic, often resulting in low Michael adduct yields due to interaction of the indolyl interaction of the indolyl hydroxy group with the Lewis acid catalyst.…”

“…In fact, the treatment of indole derivatives with α,β-disubstituted nitroalkenes in the presence of a CeCl 3 ·7H 2 O−NaI system gave the corresponding β-indolylnitroalkanes without traces of polymerization phenomena of the acid-sensitive substrates . It is known that nitroalkenes are one of the strongest Michael acceptors, providing a common pathway to nitroalkanes, which could serve as stock compounds for corresponding amino compounds . The reaction proceeds with good yields even in the case of poorly reactive indoles, and the corresponding adduct is in satisfactory yield obtained in the case of an indole derivative containing a hydroxyl group.…”

The Synthesis of Five-Membered N-Heterocycles by Cycloaddition of Nitroalkenes with (In)Organic Azides and Other 1,3-Dipoles

“…have also expanded their versatility in many organic reactions. [7][8][9][10] Cycloaddition and annulation reactions have emerged as among the most powerful methods in organic synthesis, with an ability to generate heterocycles, polyheterocycles and carbocycles with high regio-and stereoselectivity through concerted, stepwise, or sequential processes. Over the past few years, rapid growth in this area has witnessed elegant works showcasing the unique reactivity of nitroalkenes in various annulations and 1,3-dipolar cycloaddition reactions, leading to the synthesis of a range of heterocycles.…”