3653-39-2

Usage

InChI:InChI=1/C13H17NO/c15-13(12-8-4-3-5-9-12)14-10-6-1-2-7-11-14/h3-5,8-9H,1-2,6-7,10-11H2

Upstream product

• 111-49-9 hexamethylene imine 
• 98-88-4 benzoyl chloride 
• 20422-13-3 1-benzylazepane 
• 100-52-7 benzaldehyde 
• 65-85-0 benzoic acid 
• 100-51-6 benzyl alcohol 
• 93-55-0 1-phenyl-propan-1-one 
• 93-89-0 benzoic acid ethyl ester 
• 105-60-2 caprolactam 
• 93-58-3 benzoic acid methyl ester 
• 108-86-1 bromobenzene 
• 201230-82-2 carbon monoxide 

Downstream Products

• 73269-87-1 (2-Methoxy-azepan-1-yl)-phenyl-methanone 
• 956-09-2 6-(benzoylamino)hexanoic acid 
• 2163-00-0 1,6-dichlorohexane 
• 80953-69-1 1-(1-Benzoyl-azepan-2-yl)-5-fluoro-1H-pyrimidine-2,4-dione 
• 1193731-81-5 (S)-3-(4-nitrophenyl)isobenzofuran-1(3H)-one 
• 127529-25-3 C₂₀H₂₅N 
• 20422-13-3 1-benzylazepane 

Relevant academic research and scientific papers

Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates

Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.

Direct Amidation of Esters by Ball Milling**

The direct mechanochemical amidation of esters by ball milling is described. The operationally simple procedure requires an ester, an amine, and substoichiometric KOtBu and was used to prepare a large and diverse library of 78 amide structures with modest to excellent efficiency. Heteroaromatic and heterocyclic components are specifically shown to be amenable to this mechanochemical protocol. This direct synthesis platform has been applied to the synthesis of active pharmaceutical ingredients (APIs) and agrochemicals as well as the gram-scale synthesis of an active pharmaceutical, all in the absence of a reaction solvent.

Method for preparing amide compound by photocatalysis of nitrogen-containing heterocyclic compound

The invention provides a method for preparing an amide compound by photocatalysis of a nitrogen-containing heterocyclic compound. The method comprises the following steps: mixing the nitrogen-containing heterocyclic compound, organic carboxylic acid and tetrahalomethane in a solvent, adding a catalyst, and reacting under the illumination condition to prepare the amide compound. According to the invention, the organic carboxylic acid, the nitrogen-containing heterocyclic compound containing reactive hydrogen on nitrogen atoms and the tetrahalomethane are used as raw materials, so the raw materials are wide in source, low in cost and high in safety, and large-scale production is facilitated; the halogen simple substance is co-produced in the reaction process, the added value is high, a large amount of waste is prevented from being generated, and the method has high atom economy and environmental friendliness; light conditions are adopted to replace traditional heating and high-pressure conditions, the reaction conditions are mild, environmental pollution is reduced, and the reaction cost is reduced; the method has the advantages of good substrate applicability, mild process conditions, environmental protection, simple process, simple and feasible operation method, and facilitation of popularization and application.

Copper-catalyzed aerobic oxidative C-C bond cleavage of simple ketones for the synthesis of amides

A Cu-catalyzed oxidative amidation of simple ketones with amines via carbon-carbon (C-C) bond cleavage has been developed. A number of aryl and alkyl ketones could be easily converted to amides using cheap copper salt as the catalyst and O2 as the oxidant with a wide range of amines, including primary and secondary amines. This method shows a notable advantage of the broad scope for the substrate, thus providing a practical approach to amides. A plausible mechanism is proposed based on the preliminary experiments.

Synthesis method of amide compound

The invention discloses a synthesis method of an amide compound. The synthesis method comprises the following step: carrying out a photocatalytic reaction on benzyl alcohol with a structure as shown in a formula (I) and an amine compound with a structure as shown in a formula (II) in the presence of photocatalyst-loaded metal P-C3N4 by using an organic solvent as a medium to obtain the amide compound with a structure as shown in a formula (III). The synthesis method does not need a heat source for heat supply, avoids high-temperature reaction, is simple to operate, short in reaction time and simple in aftertreatment, and can easily realize industrial production.

DECONSTRUCTIVE FUNCTIONALIZATION METHODS AND COMPOUNDS

Disclosed herein, inter alia, are deconstructive functionalization methods and compounds made using the same.

Method for preparing amide compounds

The invention discloses a method for preparing amide compounds. The method comprises the step of subjecting organic carboxylate with a structure represented by a formula (I) shown in the description and an amine compound with a structure represented by a formula (II) shown in the description to a grinding reaction, thereby preparing an amide compound with a structure represented by a formula (III)shown in the description and an alcohol compound with a structure represented by a formula (IV) shown in the description. According to the synthesis method, a heat source is not required to supply heat, an organic solvent is not required to serve as a medium, the operation is simple, the reaction time is short, the aftertreatment is simple, and thus, industrial production is easy to achieve.

Frustrated Lewis Pair Catalyzed Hydrogenation of Amides: Halides as Active Lewis Base in the Metal-Free Hydrogen Activation

A method for the metal-free reduction of carboxylic amides using oxalyl chloride as an activating agent and hydrogen as the final reductant is introduced. The reaction proceeds via the hydrogen splitting by B(2,6-F2-C6H3)3 in combination with chloride as the Lewis base. Density functional theory calculations support the unprecedented role of halides as active Lewis base components in the frustrated Lewis pair mediated hydrogen activation. The reaction displays broad substrate scope for tertiary benzoic acid amides and α-branched carboxamides.

Formal Deoxygenative Hydrogenation of Lactams Using PNHP-Pincer Ruthenium Complexes under Nonacidic Conditions

A formal deoxygenative hydrogenation of amides to amines with RuCl2(NHC)(PNHP) (NHC = 1,3-dimethylimizadol-2-ylidene, PNHP = bis(2-diphenylphosphinoethyl)amine) is described. Various secondary amides, especially NH-lactams, are reduced with H2 (3.0-5.0 MPa) to amines at a temperature range of 120-150 °C with 1.0-2.0 mol % of PNHP-Ru catalysts in the presence of Cs2CO3. This process consists of (1) deaminative hydrogenation of secondary amides to generate primary amines and alcohols, (2) dehydrogenative coupling of the transient amines with alcohols to generate imines, and (3) hydrogenation of imines to give the formally deoxygenated secondary amine products.

Amide Effects in C?H Activation: Noncovalent Interactions with L-Shaped Ligand for meta Borylation of Aromatic Amides

A new concept for the meta-selective borylation of aromatic amides is described. It has been demonstrated that while esters gave para borylations, amides lead to meta borylations. For achieving high meta selectivity, an L-shaped bifunctional ligand has been employed and engages in an O???K noncovalent interaction with the oxygen atom of the moderately distorted amide carbonyl group. This interaction provides exceptional control for meta C?H activation/borylation.