38313-01-8

Upstream product

• 122-04-3 4-nitro-benzoyl chloride 
• 822-67-3 Cyclohex-2-enol 
• 110-83-8 cyclohexene 
• 62-23-7 4-nitro-benzoic acid 
• 16166-61-3 tert-butyl 4-nitrobenzoperoxoate 
• 110-82-7 cyclohexane 
• 636-97-5 N-amino-(4-nitrophenyl)carboxamide 
• 930-68-7 cyclohexenone 
• 14922-36-2 4-nitrophenylglyoxylic acid 
• 555-16-8 4-nitrobenzaldehdye 

Downstream Products

• 56391-38-9 4-Nitro-benzoic acid (1R,2S,6R)-2,6-dibromo-cyclohexyl ester 
• 103530-08-1 c-2,t-3-dibromo-r-1-cyclohexyl p-nitrobenzoate 
• 53119-31-6 t-2,c-3-dibromo-r-1-cyclohexyl p-nitrobenzoate 

Relevant academic research and scientific papers

Immobilization of (l)-valine and (l)-valinol on SBA-15 nanoporous silica and their application as chiral heterogeneous ligands in the Cu-catalyzed asymmetric allylic oxidation of alkenes

SBA-15 nanoporous silica was synthesized by hydrothermal method using P123 surfactant and tetraethoxyortosilicate in acidic condition and then functionalized by 3-chloropropyltrimethoxysilane. Next, by immobilization of chiral amino acid (S)-2-amino-3-methyl butanoic acid (l-valine) and chiral amino alcohol (S)-2-amino-3-methylbutane-1-ol (l-valinol), preparedviathe reduction ofl-valine by NaBH4/I2in THF, on functionalized-SBA-15, chiral heterogeneous ligands AL*-i-Pr-SBA-15 and AA*-i-Pr-SBA-15 were prepared and characterized by FT-IR, XRD, TGA, EDX, SEM, BET-BJH techniques. The asymmetric allylic oxidation of alkenes was done using copper-complexes of these ligands and the as-synthesized peresters. The reactions were optimized by varying various parameters such as temperature, solvent, amount of chiral heterogeneous ligand, as well as the type and amount of copper salt. Under optimized conditions, 6 mg of AL*-i-Pr-SBA-15 and 3.2 mol% of Cu(CH3CN)4PF6in acetonitrile at 50 °C, the chiral allylic ester was obtained with 80% yield and 39% enantiomeric excess in 24 h. The recyclability of the chiral heterogeneous catalysts was also evaluated without significant reduction in the reaction results up to three runs.

Effects of Silver Carbonate and p-Nitrobenzoic Acid for Accelerating Palladium-Catalyzed Allylic C-H Acyloxylation

An allylic C-H acyloxylation of terminal alkenes with 4-nitrobenzoic acid was assisted by a bidentate-sulfoxide-ligated palladium catalyst combined with 1,4-benzoquinone and Ag2CO3 under mild reaction conditions. The catalytic activity was remarkably enhanced by Ag2CO3 as an additive and 4-nitrobenzoic acid as a carboxylate source; both components were essential to exhibiting high catalytic activity, high branch selectivity, and a wide substrate scope with low loading of the palladium catalyst. Branch-selective allylic acyloxylation of ethyl 7-octenoate (1a) gave the product which was led to ethyl 6,8-dihydroxyoctanoate (5), a useful synthetic intermediate of (R)-α-lipoic acid.

Copper-iron mixed oxide supported onto cordierite honeycomb as a heterogeneous catalyst in the Kharasch-Sosnovsky oxidation of cyclohexene

A copper-iron mixed oxide was deposited by the washcoating procedure over cordierite honeycomb monoliths for its use as a heterogeneous catalyst in organic synthesis processes. In particular, the prepared catalyst, characterized by techniques such as X-ra

Late-Stage Intermolecular Allylic C-H Amination

Allylic amination enables late-stage functionalization of natural products where allylic C-H bonds are abundant and introduction of nitrogen may alter biological profiles. Despite advances, intermolecular allylic amination remains a challenging problem due to reactivity and selectivity issues that often mandate excess substrate, furnish product mixtures, and render important classes of olefins (for example, functionalized cyclic) not viable substrates. Here we report that a sustainable manganese perchlorophthalocyanine catalyst, [MnIII(ClPc)], achieves selective, preparative intermolecular allylic C-H amination of 32 cyclic and linear compounds, including ones housing basic amines and competing sites for allylic, ethereal, and benzylic amination. Mechanistic studies support that the high selectivity of [MnIII(ClPc)] may be attributed to its electrophilic, bulky nature and stepwise amination mechanism. Late-stage amination is demonstrated on five distinct classes of natural products, generally with >20:1 site-, regio-, and diastereoselectivity.

2-Aminopyrazine-functionalized MCM-41 nanoporous silica as a new efficient heterogeneous ligand for Cu-catalyzed allylic C–H bonds oxidation of olefins

In spite of the importance of the application of allylic C–H bond oxidation of olefins in organic synthesis and existence of the numerous reports, lots of limitations such as large excess of the olefin respect to the oxidant, low chemical yield, long time of reaction and a large amount of the catalyst were reminded. We introduced a novel catalytic system using functionalized MCM-41 as catalyst support to promote efficiency of this reaction. The heterogeneous ligand Pyr-MCM-41 was prepared by substituted 2-aminopyrazine ligand on functionalized MCM-41 with 3-chloropropyltrimthoxysilane and characterized by FT-IR, XRD, SEM, EDX, BET, TGA, CHN techniques. In situ immobilized Pyr-MCM-41 by copper (I) trifluoromethanesulfonate (CuOTf) was applied in direct catalytic esterification of inert C–H bonds in olefins using various peresters at room temperature.

Cu(CH3CN)4PF6 immobilized on halloysite as efficient heterogeneous catalyst for oxidation of allylic C–H bonds in olefins under mild reaction condition

Considering the importance of oxidation of allylic C–H bonds in olefins and the unresolved challenging issues, such as long reaction time and the large quantity of catalyst required, and encouraged by the excellent performance of halloysite as a catalyst

Use of CuO encapsulated in mesoporous silica SBA-15 as a recycled catalyst for allylic C-H bond oxidation of cyclic olefins at room temperature

CuO nanoparticles were deposited on SBA-15 in three routes. These were metal loading on SBA-15 and calcination at 550 °C (Cu-SBA-15), metal loading on 3-aminopropyl-trimethoxysilane grafted SBA-15 and calcination at 550 °C (Cu-N-SBA-15), and metal loading

Cobalt-catalyzed oxidative esterification of allylic/benzylic C(sp3)–H bonds

A protocol for the cobalt-catalyzed oxidative esterification of allylic/benzylic C(sp3)–H bonds with carboxylic acids was developed in this work. Mechanistic studies revealed that C(sp3)–H bond activation in the hydrocarbon was the turnover-limiting step and the in-situ formed [Co(III)]Ot-Bu did not engage in hydrogen atom abstraction (HAA) of a C–H bond. This protocol was successfully incorporated into a synthetic pathway to β-damascenone that avoided the use of NBS.

Iron-catalyzed esterification of allylic sp3 C–H bonds with carboxylic acids: Facile access to allylic esters

The first general and efficient iron-catalyzed esterification of allylic sp3 C–H bonds with carboxylic acids using ionic iron(III) complexes (1–4) as a catalyst and DTBP (DTBP?=?di-tert-butyl peroxide) as an oxidant is achieved. A variety of allylic esters were synthesized in good to excellent yields using the ionic iron(III) complex 2 as a catalyst in a 5?mol% loading. This reaction is characterized by its high efficiency, broad substrate scope with excellent steric hindrance tolerance and good functional group compatibility.

Copper-catalyzed oxidative esterification of unactivated C(sp3)-H bonds with carboxylic acids via cross dehydrogenative coupling

An effective copper-catalyzed esterification of unactivated (non-benzylic and allylic) C(sp3)-H bonds of hydrocarbons with Selectfluor as an oxidant has been developed. This reaction could provide a direct, new and useful strategy for the synthesis of esters and alkyl alcohols by ester hydrolysis.