104245-84-3

Upstream product

• 100-14-1 4-nitrobenzyl chloride 
• 107-11-9 1-amino-2-propene 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 7409-30-5 p-nitrobenzylamine 
• 27895-84-7 4-nitrobenzaldehyde N-allylimine 
• 555-16-8 4-nitrobenzaldehdye 

Downstream Products

• 1397293-49-0 5-(iodomethyl)-3-(4-nitrobenzyl)oxazolidin-2-one 
• 1418218-09-3 N-allyl-N-(4-nitrobenzyl)acrylamide 
• 1418218-40-2 1-(4-nitrobenzyl)-1H-pyrrol-2(5H)-one 
• 1453196-74-1 (S)-2-benzyl-3-methyl-5-(4-nitrobenzyl)-1,2,5-oxadiazinan-6-one 
• 1453196-56-9 (S)-N²-benzyl-N²-hydroxy-N¹-(4-nitrobenzyl)propane-1,2-diamine 
• 1383423-77-5 5-(iodomethyl)-3-(4-nitrobenzyl)thiazolidine-2-thione 

Relevant academic research and scientific papers

Nickel(II) Catalyzed Hydroboration: A Route to Selective Reduction of Aldehydes and N-Allylimines

A cationic [(iminophosphine)nickel(allyl)]+ complex was found to be sufficiently electrophilic to activate aldehydes and N-allylimines to undergo hydroboration with pinacolborane (HBpin) under mild reaction conditions. The catalyst displayed excellent selectivity toward aldehydes in the presence of ketones. A wide variety of functional groups were tolerated, including halogens, NO2, CN, OMe, and alkenes for both aldehydes and imines. Electron-rich substrates were found to be significantly more reactive than their electron poor counterparts, a feature that was correlated to their enhanced ability to coordinate to the Lewis acidic nickel center.

Carbonylative C?C Bond Activation of Electron-Poor Cyclopropanes: Rhodium-Catalyzed (3+1+2) Cycloadditions of Cyclopropylamides

Rh-catalyzed carbonylative C?C bond activation of cyclopropylamides generates configurationally stable rhodacyclopentanones that engage tethered alkenes in (3+1+2) cycloadditions. These studies provide the first examples of multicomponent cycloadditions t

Synthesis of Cyclic N-Hydroxylated Ureas and Oxazolidinone Oximes Enabled by Chemoselective Iodine(III)-Mediated Radical or Cationic Cyclizations of Unsaturated N-Alkoxyureas

In this study we describe the reactivity of unsaturated N-alkoxyureas in the presence of different combinations of a hypervalent iodine(III) reagent and a bromide source or TEMPO. Three complementary cyclizations can be achieved depending on the reaction conditions. On the one hand, PIFA with pyridinium bromide leads to an oxybromination reaction. On the other hand, bis(tert-butylcarbonyloxy)iodobenzene with tetrabutylammonium bromide or TEMPO triggers aminobromination or aminooxyamination reactions, respectively. Control experiments showed that the three reactions proceed through distinct mechanisms: the first process is ionic while the other two follow a radical manifold. (Figure presented.).

Selective hydrosilylation of N-allylimines using a (3-iminophosphine)palladium precatalyst

Hydrosilylation utilizing a (3-iminophosphine)palladium catalyst leads to the selective reduction of the imine unit of allylimines. Successful reduction of twenty-five different substituted aromatic and alkyl allylimines demonstrated the scope and selecti

Palladium-catalyzed vicinal amino alcohols synthesis from allyl amines by in situ tether formation and carboetherification

Vicinal amino alcohols are important structural motifs of bioactive compounds. Reported herein is an efficient method for their synthesis based on the palladium-catalyzed oxy-alkynylation, oxy-arylation, or oxy-vinylation of allylic amines. High regio- and stereoselectivity were ensured through the in situ formation of a hemiaminal tether using the cheap commercially available trifluoroacetaldehyde in its hemiacetal form. The obtained compounds are important building blocks, which can be orthogonally deprotected to give either free alcohols, amines, or terminal alkynes.

Ring-closing metathesis of vinyl fluorides towards α-fluorinated α,β-unsaturated lactams and lactones

Ring-closing olefin metathesis reactions (RCM) using Grubbs II or Hoveyda's catalysts have been applied to a series of N-alkenyl-N-benzyl-α-fluoroacrylamides. α-Fluoro-α,β-unsaturated γ- or δ-lactams incorporating a fluorinated double bond were obtained in moderate to good yields, depending on the nature of substituents on the benzyl ring. The corresponding seven- and eight-membered lactams were not formed under similar conditions. When the N-benzyl group was replaced by an N-tosyl group, the corresponding ε-lactam was also formed in 38% yield. When N-(2-fluoroallyl) derivatives were used instead of fluoroacryloyl derivatives, six-, seven-, and eight-membered N-heterocycles were obtained in low yields. This method was also used to synthesize fluorinated α,β-unsaturated analogues of pyrrolizidine and indolizidine alkaloids from prolinol, and also to synthesize N-benzyl-3-fluoroquinolone in three steps from commercially available 2-vinylaniline in 44% overall yield. Also 3-fluorocoumarin and 3-fluorochromene were prepared from ovinylphenol, and 3-fluoro-benzoxepine was available from o-allylphenol.

Highly enantioselective intermolecular hydroamination of allylic amines with chiral aldehydes as tethering catalysts

Chirally LinkedIn: Chiral aldehydes are effective tethering catalysts for enantioselective intermolecular hydroamination, which provides access to vicinal diamine motifs in good yields and excellent enantioselectivities (see scheme). This work highlights simple chiral α-oxygenated aldehydes as effective organocatalysts capable of efficiently inducing asymmetry through transient intramolecularity. Copyright

A one-pot, three-component synthesis of thiazolidine-2-thiones

An efficient method for the synthesis of thiazolidine-2-thiones is described via regiospecific iodocyclization of an allyl amine, carbon disulfide, and iodine. Dehydrohalogenation of the iodo-derivatives gives thiazole-2(3H)-thiones. In addition, nucleoph

Synthesis of nitrogen-containing heterocycles via ring-closing ene-ene and ene-yne metathesis reactions: An easy access to 1- and 2-benzazepine scaffolds and five- and six-membered lactams

Novel regioselective ring closing ene-yne metathesis provided an efficient access to different substituted 1-benzazepine scaffolds. The reported synthetic approach could also be used as a powerful tool for the selective formation of a highly functionaliza

Cyclizative atmospheric CO2 fixation by unsaturated amines with t-BuOI leading to cyclic carbamates

A cyclizative atmospheric CO2 fixation by unsaturated amines such as allyl and propargyl amines under mild reaction conditions, efficiently leading to cyclic carbamates bearing a iodomethyl group, have been developed utilizing tert-butyl hypoiodite (t-BuOI).