123464-38-0

Upstream product

• 1135-99-5 diphenyltin(IV) dichloride 
• 50598-92-0 (E)-(2-nitrovinyl)cyclohexane 
• 5153-67-3 nitrostyrene 
• 626-62-0 Cyclohexyl iodide 
• 50598-92-0 2-cyclohexyl-1-nitroethene 
• 98-80-6 phenylboronic acid 
• 595-90-4 tetraphenyltin(IV) 
• 780-69-8 triethoxyphenylsilane 
• 102-96-5 (2-nitroethenyl)benzene 

Relevant academic research and scientific papers

Deoxycholic acid-derived biaryl phosphites as versatile and enantioselective ligands in the rhodium-catalyzed conjugate addition of arylboronic acids to nitroalkenes

A highly enantioselective conjugate addition of arylboronic acids to cyclic as well as acyclic aromatic and aliphatic nitroalkenes is presented. The rhodium complexes obtained from deoxycholic acid-derived binaphthyl and flexible biphenyl phosphites showed good activity as well as very high enantioselectivity (ee up to 99%) in the conjugated addition even in the presence of challenging substrates such as 1-nitrocyclohexene or aliphatic acyclic nitroalkenes. Copyright

Conjugate Addition of Organozinc Compounds to Nitroolefins

Symmetrical (R2Zn) or mixed diorganozinc compounds (R 1ZnR2) smoothly react with a series of nitroolefins in the presence of catalytic amounts of copper(I) salts and provide synthetically versatile nitro compounds in moderate to good yields. Simple alkyl groups, functionalized residues, or mixed trimethylsilylmethyl organozinc compounds (TMSM)ZnR may be employed for conjugate addition, while the TMSM group is not being transferred. ipso-Substitution is observed in absence of the copper(I) salt. Enantiomerically pure copper(I) complexes with BINOL based chiral phosphoramidite ligands efficiently catalyze the addition of dialkylzinc compounds to nitroalkenes. For instance, diethylzinc addition occurs with high yields and excellent enantioselectivity. Nitrostyrene, 3-nitroacrolein dimethylacetal, and 3-nitroacrylates have been used as substrates. The nitroolefin moiety predominates over the acrylate moiety and acts as the more powerful Michael acceptor. 2-Alkyl-3-nitropropanoates are exclusively obtained with excellent yield and enantioselectivity. The products can easily be transformed into β2-homoamino acids, compounds of high relevance for different areas of preparative organic chemistry.

Palladium(II)-catalyzed Michael-type hydroarylation of nitroalkenes using aryltins and sodium tetraarylborates

A variety of aryltin compounds and sodium tetraarylborates can be employed for Michael-type hydroarylation reactions of nitroalkenes to afford β-arylnitroalkanes in moderate to good yields in the presence of either LiCl, MgCl2, or CaCl2 and a catalytic amount of palladium(II) salt (0.05 molar amount) in acetic acid. Results show that 50-70% of aryl groups out of all in these aryl compounds can be transferred to the products in this hydroarylation. The addition of a catalytic amount (0.05-0.10 molar amount) of a Lewis acid chloride, BiCl3 or SbCl3, much improves the product yield in some cases.

Palladium-catalyzed conjugate addition of organosiloxanes to α,β-unsaturated carbonyl compounds and nitroalkenes

The addition of aryltrialkoxysilanes to α,β-unsaturated carbonyl compounds (ketones, aldehydes) and nitroalkenes in the presence of SbCl3, TBAF, AcOH, and a catalytic amount of Pd(OAc)2, in CH3CN at 60 °C, provides the corresponding conjugate addition products in moderate to good yields. The addition of equimolar amounts of SbCl3 and TBAF is necessary for this reaction to proceed smoothly. The arylpalladium complex, which is generated by the transmetalation from a putative hypercoordinate silicon compound, is considered to be the catalytically active species.

Conjugate addition of mixed diorganozinc compounds and functionalized organozinc cuprates to nitroolefins

equation presented The copper-catalyzed conjugate addition of symmetrical and mixed diorganozinc compounds as well as functionalized diorganozinc cuprates to nitroolefins leads to synthetically versatile nitro compounds in moderate to good yields. Mixed TMSM-organozinc compounds are suitable reagents for conjugate addition, since the TMSM group is not being transferred. Ipso substitution is observed in the absence of a catalytic amount of copper(I) salt. The nitroalkene moiety in 3-nitroacrylates proved to be the predominant Michael acceptor.

Preparation of Polyfunctional Nitro Olefins and Nitroalkanes Using the Copper-Zinc Reagents RCu(CN)ZnI

The addition of the copper-zinc reagents RCu(CN)ZnX to a variety of nitro olefins produces polyfunctional nitroalkanes in high yields.The intermediate zinc or copper nitronates can be directly submitted to a Nef reaction (O3, -78 deg C) and converted to p

The Addition of the Highly Functionalized Zinc, Copper Reagents RCu(CN)ZnI to Nitro Olefins

The addition of the highly functionalized zinc and copper organometallics FG-RCu(CN)ZnI to nitro olefins furnishes polyfunctional nitroalkanes in good to excellent yields; with α-substituted nitro olefins, the Michael adducts can be directly converted int