82082-48-2

Upstream product

• 586-38-9 3-Methoxybenzoic acid 
• 100-46-9 benzylamine 
• 766-85-8 3-methoxy-1-iodobenzene 
• 29139-30-8 benzylaminepentacarbonylmolybdenum 
• 5813-86-5 m-methoxybenzamide 
• 1711-05-3 m-anisoyl chloride 
• 35692-26-3 3-trimethoxyphenyltrimethoxysilane 
• 10365-98-7 3-methoxyphenylboronic acid 
• 1239497-28-9 N-benzyl-2,2-difluoro-2-iodoacetamide 
• 325142-84-5 3-methoxyphenylboronic acid pinacol ester 
• 24475-94-3 1-(3-methoxyphenyl)-3-phenylprop-2-yn-1-one 
• 6971-51-3 3-methoxybenzyl alcohol 
• 591-31-1 3-methoxy-benzaldehyde 
• 622-79-7 benzyl azide 

Downstream Products

• 15789-02-3 N-benzyl-3-hydroxybenzamide 
• 1347749-17-0 2-benzyl-5-methoxybenzo[d][1,2]selenazol-3(2H)-one 
• 1347749-16-9 2-benzyl-7-methoxybenzo[d][1,2]selenazol-3(2H)-one 

Relevant academic research and scientific papers

Synthesis of Benzoisoselenazolones via Rh(III)-Catalyzed Direct Annulative Selenation by Using Elemental Selenium

Isoselenazolone derivatives have attracted significant research interest because of their potent therapeutic activities and indispensable applications in organic synthesis. Efficient construction of functionalized isoselenazolone scaffolds is still challenging, and thus new synthetic approaches with improved operational simplicity have been of particular interest. In this manuscript, we introduce a rhodium-catalyzed direct selenium annulation by using stable and tractable elemental selenium. A series of benzamides as well as acrylamides were successfully coupled with selenium under mild reaction conditions, and the obtained isoselenazolones could be pivotal synthetic precursors for several organoselenium compounds. Based on the designed control experiments and X-ray absorption spectroscopy measurements, we propose an unprecedented selenation mechanism involving a highly electrophilic Se(IV) species as the reactive selenium donor. The reaction mechanism was further verified by a computational study.

Cu-catalyzed arylation of bromo-difluoro-acetamides by aryl boronic acids, aryl trialkoxysilanes and dimethyl-aryl-sulfonium salts: New entries to aromatic amides

We describe a mechanism-guided discovery of a synthetic methodology that enables the preparation of aromatic amides from 2-bromo-2, 2-difluoroacetamides utilizing a copper-catalyzed direct arylation. Readily available and structurally simple aryl precursors such as aryl boronic acids, aryl trialkoxysilanes and dimethyl-aryl-sulfonium salts were used as the source for the aryl substituents. The scope of the reactions was tested, and the reactions were insensitive to the electronic nature of the aryl groups, as both electron-rich and electron-deficient aryls were successfully introduced. A wide range of 2-bromo-2, 2-difluoroacetamides as either aliphatic or aromatic secondary or tertiary amides were also reactive under the developed conditions. The described synthetic protocols displayed excellent efficiency and were successfully utilized for the expeditious preparation of diverse aromatic amides in good-to-excellent yields. The reactions were scaled up to gram quantities.

Hydrogen Bond Directed ortho-Selective C?H Borylation of Secondary Aromatic Amides

Reported is an iridium catalyst for ortho-selective C?H borylation of challenging secondary aromatic amide substrates, and the regioselectivity is controlled by hydrogen-bond interactions. The BAIPy-Ir catalyst forms three hydrogen bonds with the substrate during the crucial activation step, and allows ortho-C?H borylation with high selectivity. The catalyst displays unprecedented ortho selectivities for a wide variety of substrates that differ in electronic and steric properties, and the catalyst tolerates various functional groups. The regioselective C?H borylation catalyst is readily accessible and converts substrates on gram scale with high selectivity and conversion.

Base-promoted amide synthesis from aliphatic amines and ynones as acylation agents through C-C bond cleavage

A new protocol for the synthesis of amides via base-promoted cleavage of the C(sp)-C(CO) bond of ynones with aliphatic primary and secondary amines under transition-metal-, ligand-, and oxidant-free conditions has been developed. This method exhibits a wide substrate scope, high functional group tolerance and exclusive chemoselectivity, as well as mild reaction conditions.

Ruthenium(II) complexes encompassing 2-oxo-1,2-dihydroquinoline-3-carbaldehyde thiosemicarbazone hybrid ligand: A new versatile potential catalyst for dehydrogenative amide synthesis

Ruthenium(II) complexes (1–6) supported by a series of 2-oxo-1,2-dihydroquinoline-3-carbaldehyde substituted thiosemicarbazone ligands [2-oxo-1,2-dihydroquinoline-3-carbaldehyde thiosemicarbazone (L1), 2-oxo-1,2-dihydroquinoline-3-carbaldehyde N-methyl thiosemicarbazone (L2), 2-oxo-1,2-dihydroquinoline-3-carbaldehyde N-phenylthiosemicarbazone (L3)] have been synthesized and structurally characterized by analytical, spectroscopic methods and X-ray crystallographic technique. The studies revealed that the ligands act as mononegative tridentate in ruthenium(II) complexes and a distorted octahedral geometry has been proposed for the complexes. In addition, the complexes have been found to catalyze the amidation of alcohols with amines in the presence of KtBuO–toluene system. The catalyst 3 displayed higher activity in substrates, including phenyl-, pyridine-, furan-, and thiophene-substituted alcohols with primary and secondary amines. The protocol is highly attractive because of easily available starting materials, high atom efficiency and environmental friendliness.

Transamidation of carboxamides with amines over nanosized zeolite beta under solvent-free conditions

A highly efficient approach to transamidation of carboxamides with amines over nanosized zeolite beta under solvent-free conditions has been successfully demonstrated. Transamidation of a variety of amides with amines produced the respective N-alkyl amides in moderate to excellent yields.

Ruthenium(II) carbonyl complexes containing bidentate 2-oxo-1,2-dihydroquinoline-3-carbaldehyde hydrazone ligands as efficient catalysts for catalytic amidation reaction

The coordination behavior of 2-oxo-1,2-dihydroquinoline-3-carbaldehyde hydrazone ligands in ruthenium(II) and the catalytic activity of newly synthesized complexes have been studied. The complexes [RuCl(CO)(PPh3)2(L1)] (1), [RuCl(CO)(AsPh3)2(L1)] (2), [RuCl(CO)(PPh3)2(L2)] (3) and [RuCl(CO)(AsPh3)2(L2)] (4) were synthesized by reactions of [RuHCl(CO)(EPh3)3] (E = P or As) precursors with hydrazone ligands and characterized by analytical and spectroscopic methods. The molecular structure of complex 2 was identified by means of single-crystal X-ray diffraction analysis. The structural analysis revealed that all the complexes possess a distorted octahedral geometry with the ligand coordinating in a uni-negative bidentate NO fashion. Further, the catalytic efficiency of the complexes have been investigated in the case of direct amidation of alcohols with amines. The influence of base, reaction temperature and catalyst loading in the amidation reaction was also evaluated. Notably, complex 3 was found to be very efficient catalyst towards amidation of alcohols with amine. A variety of aromatic (hetero) amines and alcohols with various functional groups have also been successfully used for amidations.

C-N Coupling of Amides with Alcohols Catalyzed by N-Heterocyclic Carbene-Phosphine Iridium Complexes

N-Heterocyclic carbene-phosphine iridium complexes (NHC-Ir) were developed/found to be a highly reactive catalyst for N-monoalkylation of amides with alcohols via hydrogen transfer. The reaction produced the desired product in high isolated yields using a wide range of substrates with low catalyst loading and short reaction times.

A simple base-mediated amidation of aldehydes with azides

A practical and efficient amidation reaction involving aromatic aldehydes and various azides under mild conditions is described. A broad spectrum of functional groups was tolerated, and the amides were synthesized in moderate to excellent yields, presenting an attractive alternative to the currently available synthetic methods.

Organic ligand-free alkylation of amines, carboxamides, sulfonamides, and ketones by using alcohols catalyzed by heterogeneous Ag/Mo oxides

Complicated and expensive organic ligands are normally essential in fine chemical synthesis at preparative or industrial levels. The synthesis of fine chemicals by using heterogeneous catalyst systems without additive organic ligand is highly desirable but severely limited due to their poor generality and rigorous reaction conditions. Here, we show the results of carbon-nitrogen or carbon-carbon bond formation catalyzed by an Ag/Mo hybrid material with specific Ag6Mo10O33 crystal structure. 48 nitrogen- or oxygen-containing compounds, that is, amines, carboxamides, sulfonamides, and ketones, were successfully synthesized through a borrowing-hydrogen mechanism. Up to 99% isolated yields were obtained under relatively mild conditions without additive organic ligand. The catalytic process shows promise for the efficient and economic synthesis of amine, carboxamide, sulfonamide, and ketone derivatives because of the simplicity of the system and ease of operation. Copyright