14367-96-5

Upstream product

• 3132-99-8 m-bromobenzoic aldehyde 
• 75-52-5 nitromethane 
• 91240-83-4 1-(3-bromo-benzoyl)-1H-imidazole 
• 585-76-2 m-bromobenzoic acid 
• 25854-38-0 sodium nitromethane 
• 39220-96-7 1-(3-bromophenyl)-2-nitroethanol 
• 314767-38-9 (1H-benzo[d][1,2,3]triazol-1-yl)(3-bromophenyl)methanone 

Downstream Products

• 1194628-13-1 5-(3-bromophenyl)-2-phenyloxazole 
• 1100273-65-1 (S)-(+)-1-(3-bromophenyl)-2-nitroethanol 
• 618-89-3 methyl 3-bromobenzoate 
• 630050-32-7 3-bromo-N-(4-methylbenzenesulfonyl)benzenecarboxamide 
• 74048-09-2 2-methyl-5-(m-bromophenyl)oxazole 
• 1044833-29-5 (R)-(-)-1-(3-bromophenyl)-2-nitroethanol 
• 745079-14-5 ethyl 5-(3-bromophenyl)-4-nitroisoxazole-3-carboxylate 
• 14547-41-2 1-(3-bromo-phenyl)-3-morpholin-4-yl-2-nitro-propan-1-one 

Relevant academic research and scientific papers

Facile synthesis of 2-nitromethyl aromatic ketones by insertion of benzynes into the C-C bond of α-nitroketones

A facile method to synthesize 2-nitromethyl aromatic ketones was developed. In the method, benzyne was generated in situ for the insertion to α-Nitroketones in one pot to achieve 2-nitromethyl aromatic ketones under mild conditions. Aromatic and aliphatic α-nitroketones were applied in the reaction, and the results show that aliphatic α-nitroketones gave excellent yields (up to 96%), while aromatic α-nitroketones gave moderate yields. The synthesized 2-nitromethyl aromatic ketones could be potential substrates to synthesize isoindoles.

α-Nitro-α,β-Unsaturated Ketones: An Electrophilic Acyl Transfer Reagent in Catalytic Asymmetric Friedel-Crafts and Michael Reactions

Herein, we introduce α-nitro-α,β-unsaturated ketones as efficient electrophilic acyl transfer reagents, and they were employed in Friedel-Crafts as well as in Michael reactions. The desired acyl transfer products of these reactions were obtained in high yields with high to excellent enantioselectivities with t-leucine-derived squaramide catalyst under mild reaction conditions. Few applications including a synthesis of the isoxazoline motif have been demonstrated.

Organocatalytic Asymmetric Domino Michael/Acyl Transfer Reaction Between α-Nitroketones and in situ-Generated ortho-Quinone Methides: Route to 2-(1-Arylethyl)phenols

An organocatalytic asymmetric domino Michael/acyl transfer reaction between α-nitroketones and o-quinone methides is disclosed. o-Quinone methides are generated in situ from 2-sulfonylmethylphenols in basic medium. With 10 mol% of bifunctional squaramide catalyst, high yields and excellent enantioselectivities are achieved for a variety of O-acyl 2-(1-arylethyl)phenols under mild reaction condition. (Figure presented.).

Asymmetric Bioreduction of β-Acylaminonitroalkenes: Easy Access to Chiral Building Blocks with Two Vicinal Nitrogen-Containing Functional Groups

The reduction of (Z)-β-acylaminonitroalkenes catalyzed by ene-reductases is described for the first time. The reaction occurs with a high conversion and excellent enantioselectivity and shows a wide substrate scope. The reduced products are valuable chiral synthons characterized by two vicinal nitrogen-containing functional groups that can be further modified by functional group inter-conversion thanks to the synthetic versatility of the nitro moiety. The chemo-enzymatic synthesis of (R)-N,N′-(1-phenylethane-1,2-diyl)diacetamide from easily accessible (Z)-N-(2-nitro-1-phenylvinyl)acetamide is herein reported as a representative application of this synthetic procedure.

Unexpected C-C bond cleavage of α-nitroketone in the presence of TsNBr2: A new pathway for C-N bond formation

A new catalyst-free protocol for C-N bond formation via the cleavage of α-nitroketone has been developed. When α-nitroketones are treated with TsNBr2 in the presence of potassium carbonate, unexpected cleavage of C(O)-CHNO2 bond of α-nitroketone was observed followed by the formation of corresponding amide. Various nitroketones could be converted to corresponding amide using this procedure.

Formation of new C-O and C-N bonds via base promoted Csp2-Csp3 bond cleavage of α-nitro ketone

A catalyst free protocol has been developed for nucleophilic Csp2-Csp3 bond cleavage of α-nitroketone in the presence of potassium carbonate to create new C-O and C-N bonds. A series of different substituted α-nitroketones could be selectively cleaved and converted into corresponding esters and tosylamides in the presence of alcohols and bromamine-T, respectively.

Rhodium-catalyzed enantioselective hydrogenation of β-acylamino nitroolefins: A new approach to chiral β-amino nitroalkanes

An efficient and highly enantioselective catalytic asymmetric hydrogenation of β-acylamino nitroolefins has been realized by using Rh-TangPhos as the catalyst. A series of β-amino nitroalkane products, which are versatile intermediates in organic synthesis, were obtained with high yield and good enantioselectivity.

Iridium diamine catalyst for the asymmetric transfer hydrogenation of ketones

A simple and very efficient chiral aqua iridium(III) diamine complex leads to excellent enantioselectivities in the asymmetric transfer hydrogenation of various α-cyano and α-nitro ketones. The catalyst provides the ortho-substituted aromatic alcohols with especially high ee values. The diamine ligands can be used directly as chiral ligands; conversion into the corresponding sulfamide is not necessary.

Transfer hydrogenation in water: Enantioselective, catalytic reduction of α-cyano and α-nitro substituted acetophenones

Catalytic reduction of α-substituted acetophenones under conditions involving asymmetric transfer hydrogenation in water is described. The reaction is conducted in water and open to air, and formic acid is used as reductant.

Indium-mediated one-pot synthesis of benzoxazoles or oxazoles from 2-nitrophenols or 1-aryl-2-nitroethanones

One-pot reduction-triggered heterocyclizations from 2-nitrophenols to benzoxazoles and from 1-aryl-2-nitroethanones to oxazoles were investigated. In the presence of indium/AcOH in benzene at reflux, 2-nitrophenols and R-C(OMe)3 (R=H, Me, Ph) produced excellent yields of corresponding benzoxazoles within an hour. Similarly, 1-aryl-2-nitroethanones and Ph-C(OMe)3 in the presence of indium/AcOH in acetonitrile transformed into the corresponding oxazoles with good yields.