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Relevant academic research and scientific papers

Iron-Catalyzed Mild and Selective Hydrogenative Cross-Coupling of Nitriles and Amines To Form Secondary Aldimines

The first example of a base-metal-catalyzed homogeneous hydrogenative coupling of nitriles and amines to selectively form secondary cross-imines is reported. The reaction is catalyzed under mild conditions by a well-defined (iPr-PNP)Fe(H)Br(CO) pincer pre-catalyst and catalytic tBuOK.

MANGANESE BASED COMPLEXES AND USES THEREOF FOR HOMOGENEOUS CATALYSIS

The present invention relates to novel manganese complexes and their use, inter alia, for homogeneous catalysis in (1) the preparation of imine by dehydrogenative coupling of an alcohol and amine; (2) C-C coupling in Michael addition reaction using nitriles as Michael donors; (3) dehydrogenative coupling of alcohols to give esters and hydrogen gas (4) hydrogenation of esters to form alcohols (including hydrogenation of cyclic esters (lactones) or cyclic di-esters (di- lactones), or polyesters); (5) hydrogenation of amides (including cyclic dipeptides, lactams, diamide, polypeptides and polyamides) to alcohols and amines (or diamine); (6) hydrogenation of organic carbonates (including polycarbonates) to alcohols or hydrogenation of carbamates (including polycarbamates) or urea derivatives to alcohols and amines; (7) dehydrogenation of secondary alcohols to ketones; (8) amidation of esters (i.e., synthesis of amides from esters and amines); (9) acylation of alcohols using esters; (10) coupling of alcohols with water and a base to form carboxylic acids; and (11) preparation of amino acids or their salts by coupling of amino alcohols with water and a base. (12) preparation of amides (including formamides, cyclic dipeptides, diamide, lactams, polypeptides and polyamides) by dehydrogenative coupling of alcohols and amines; (13) preparation of imides from diols.

Tunable Ligand Effects on Ruthenium Catalyst Activity for Selectively Preparing Imines or Amides by Dehydrogenative Coupling Reactions of Alcohols and Amines

Selective dehydrogenative synthesis of imines from a variety of alcohols and amines was developed by using the ruthenium complex [RuCl2(dppea)2] (6 a: dppea=2-diphenylphosphino-ethylamine) in the presence of catalytic amounts of Zn(OCOCF3)2 and KOtBu, whereas the selective dehydrogenative formation of amides from the same sources was achieved by using another ruthenium complex, [RuCl2{(S)-dppmp}2] [6 d: (S)-dppmp=(S)-2-((diphenylphosphenyl)methyl)pyrrolidine], in the presence of catalytic amounts of Zn(OCOCF3)2 and potassium bis(trimethylsilyl)amide (KHMDS). Our previously reported ruthenium complex, [Ru(OCOCF3)2(dppea)2] (8 a), was the catalyst precursor for the imine synthesis, whereas [Ru(OCOCF3)2{(S)-dppmp}2] (8 d), which was derived from the treatment of 6 d with Zn(OCOCF3)2 and characterized by single-crystal X-ray analysis, was the pre-catalyst for the amide formation. Control experiments revealed that the zinc salt functioned as a reagent for replacing chloride anions with trifluoroacetate anions. Plausible mechanisms for both selective dehydrogenative coupling reactions are proposed based on a time-course study, Hammett plot, and deuterium-labeling experiments.

Manganese-Catalyzed Environmentally Benign Dehydrogenative Coupling of Alcohols and Amines to Form Aldimines and H2: A Catalytic and Mechanistic Study

The catalytic dehydrogenative coupling of alcohols and amines to form aldimines represents an environmentally benign methodology in organic chemistry. This has been accomplished in recent years mainly with precious-metal-based catalysts. We present the dehydrogenative coupling of alcohols and amines to form imines and H2 that is catalyzed, for the first time, by a complex of the earth-abundant Mn. Detailed mechanistic study was carried out with the aid of NMR spectroscopy, intermediate isolation, and X-ray analysis.

Ionic liquid effects on a multistep process. Increased product formation due to enhancement of all steps

The reaction of a series of substituted benzaldehydes with hexylamine was examined in acetonitrile and an ionic liquid. In acetonitrile, as the electron withdrawing nature of the substituent increases, the overall addition-elimination process becomes fast

Efficient tandem synthesis of methyl esters and imines by using versatile hydrotalcite-supported gold nanoparticles

Efficient basic hydrotalcite (HT)-supported gold nanoparticle (AuNP) catalysts have been developed for the aerobic oxidative tandem synthesis of methyl esters and imines from primary alcohols catalyzed under mild and soluble-base-free conditions. The catalytic performance can be fine-tuned for these cascade reactions by simple adjustment of the Mg/Al atomic ratio of the HT support. The one-pot synthesis of methyl esters benefits from high basicity (Mg/Al=5), whereas moderate basicity greatly improves imine selectivity (Mg/Al=2). These catalysts outperform previously reported AuNP catalysts by far. Kinetic studies show a cooperative enhancement between AuNP and the surface basic sites, which not only benefits the oxidation of the starting alcohol but also the subsequent steps of the tandem reactions. To the best of our knowledge, this is the first time that straightforward control of the composition of the support has been shown to yield optimum AuNP catalysts for different tandem reactions. Copyright

Microwave-assisted oxidative coupling of amines to imines on solid acid catalysts

A K-10 montmorillonite catalyzed microwave-assisted oxidative coupling of amines is described. Substituted benzylamines readily undergo self-coupling reactions to produce benzylidene-benzylamines, while aliphatic amines and anilines cannot form self-coupl