7474-36-4Relevant academic research and scientific papers
Synthesis and characterization of Pd(II)–vitamin B6 complex supported on magnetic nanoparticle as an efficient and recyclable catalyst system for C–N cross coupling of amides in deep eutectic solvents
Bagheri, Sepideh,Pazoki, Farzane,Esfandiary, Naghmeh,Fadaei, Mohammad Mahdi,Heydari, Akbar
, (2020/06/04)
Vitamin B6–Pd(II) immobilized onto magnetic nanoparticles have been successfully prepared and applied for C–Xcross-coupling reactions with aryl halides in green deep eutectic solvents. The results prove that the Fe3O4@vitamin B6–Pd(II) magnetic nanoparticles show high catalyst activity and good stability. It was also revealed that this complex can be recycled up to five times without any significant loss in catalytic activity.
Tandem Photoredox Catalysis: Enabling Carbonylative Amidation of Aryl and Alkylhalides
Connell, Timothy U.,Forni, José A.,Micic, Nenad,Polyzos, Anastasios,Weragoda, Geethika
supporting information, p. 18646 - 18654 (2020/08/21)
We report a new visible-light-mediated carbonylative amidation of aryl, heteroaryl, and alkyl halides. A tandem catalytic cycle of [Ir(ppy)2(dtb-bpy)]+ generates a potent iridium photoreductant through a second catalytic cycle in the presence of DIPEA, which productively engages aryl bromides, iodides, and even chlorides as well as primary, secondary, and tertiary alkyl iodides. The versatile in situ generated catalyst is compatible with aliphatic and aromatic amines, shows high functional-group tolerance, and enables the late-stage amidation of complex natural products.
Preparation method of fatty acid amide
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Paragraph 0052, (2019/02/13)
The invention relates to a preparation method of fatty acid amide. The method includes: adding hydroxylamine hydrochloride, a transition metal, a phosphine ligand, olefin and a solvent into a high pressure reaction kettle in order, carrying out hydroamine
Nickel-catalyzed transamidation of aliphatic amide derivatives
Dander, Jacob E.,Baker, Emma L.,Garg, Neil K.
, p. 6433 - 6438 (2017/08/29)
Transamidation, or the conversion of one amide to another, is a long-standing challenge in organic synthesis. Although notable progress has been made in the transamidation of primary amides, the transamidation of secondary amides has remained underdeveloped, especially when considering aliphatic substrates. Herein, we report a two-step approach to achieve the transamidation of secondary aliphatic amides, which relies on non-precious metal catalysis. The method involves initial Boc-functionalization of secondary amide substrates to weaken the amide C-N bond. Subsequent treatment with a nickel catalyst, in the presence of an appropriate amine coupling partner, then delivers the net transamidated products. The transformation proceeds in synthetically useful yields across a range of substrates. A series of competition experiments delineate selectivity patterns that should influence future synthetic design. Moreover, the transamidation of Boc-activated secondary amide derivatives bearing epimerizable stereocenters underscores the mildness and synthetic utility of this methodology. This study provides the most general solution to the classic problem of secondary amide transamidation reported to date.
Nickel/Photoredox-Catalyzed Amidation via Alkylsilicates and Isocyanates
Zheng, Shuai,Primer, David N.,Molander, Gary A.
, p. 7957 - 7961 (2017/11/10)
A nickel/photoredox, dual-catalyzed amidation reaction between alkylsilicate reagents and alkyl/aryl isocyanates is reported. In contrast to the previously reported reductive coupling process, this protocol is characterized by mild reaction conditions and the absence of a stoichiometric reductant. A mechanistic hypothesis involving a nickel-isocyanate adduct is proposed based on literature precedent and further validation by experimental results.
Mild and Low-Pressure fac-Ir(ppy)3-Mediated Radical Aminocarbonylation of Unactivated Alkyl Iodides through Visible-Light Photoredox Catalysis
Chow, Shiao Y.,Stevens, Marc Y.,?kerbladh, Linda,Bergman, Sara,Odell, Luke R.
supporting information, p. 9155 - 9161 (2016/07/14)
A novel, mild and facile preparation of alkyl amides from unactivated alkyl iodides employing a fac-Ir(ppy)3-catalyzed radical aminocarbonylation protocol has been developed. Using a two-chambered system, alkyl iodides, fac-Ir(ppy)3, amines, reductants, and CO gas (released ex situ from Mo(CO)6), were combined and subjected to an initial radical reductive dehalogenation generating alkyl radicals, and a subsequent aminocarbonylation with amines affording a wide range of alkyl amides in moderate to excellent yields.
Copper-Catalyzed Carbonylative Synthesis of Aliphatic Amides from Alkanes and Primary Amines via C(sp3)-H Bond Activation
Li, Yahui,Zhu, Fengxiang,Wang, Zechao,Wu, Xiao-Feng
, p. 5561 - 5564 (2016/08/18)
Amides are important intermediates and building blocks in organic synthesis. Among the known preparation procedures, aminocarbonylation is an interesting and powerful tool. However, most of the studies were focused on noble metal-catalyzed synthesis of ar
Photoinduced, copper-catalyzed alkylation of amides with unactivated secondary alkyl halides at room temperature
Do, Hien-Quang,Bachman, Shoshana,Bissember, Alex C.,Peters, Jonas C.,Fu, Gregory C.
supporting information, p. 2162 - 2167 (2014/03/21)
The development of a mild and general method for the alkylation of amides with relatively unreactive alkyl halides (i.e., poor substrates for S N2 reactions) is an ongoing challenge in organic synthesis. We describe herein a versatile transition-metal-catalyzed approach: in particular, a photoinduced, copper-catalyzed monoalkylation of primary amides. A broad array of alkyl and aryl amides (as well as a lactam and a 2-oxazolidinone) couple with unactivated secondary (and hindered primary) alkyl bromides and iodides using a single set of comparatively simple and mild conditions: inexpensive CuI as the catalyst, no separate added ligand, and C-N bond formation at room temperature. The method is compatible with a variety of functional groups, such as an olefin, a carbamate, a thiophene, and a pyridine, and it has been applied to the synthesis of an opioid receptor antagonist. A range of mechanistic observations, including reactivity and stereochemical studies, are consistent with a coupling pathway that includes photoexcitation of a copper-amidate complex, followed by electron transfer to form an alkyl radical.
Pseudomonas stutzeri lipase: A useful biocatalyst for aminolysis reactions
Van Pelt,Teeuwen,Janssen,Sheldon,Dunn,Howard,Kumar,Martinez,Wong
experimental part, p. 1791 - 1798 (2011/10/09)
The use of Pseudomonas stutzeri lipase (PSL) as a biocatalyst for aminolysis reactions with bulky substrates has been investigated. PSL compared favorably to Novozym 435 (immobilized Candida antarctica lipase B, NOV435) in the aminolysis of various bulky methyl esters and amines. While NOV435 demonstrated a higher rate of aminolysis with methyl 2-phenylpropionic acid as the acyl donor, PSL outperformed NOV435 with secondary amines as the nucleophile. Methanol inhibition and a low affinity for bulky acyl donors were found to be the two main reasons for relatively low rates in the PSL-catalyzed aminolysis reactions. It was demonstrated that the use of molsieve 4A had a significant effect on the aminolysis rate and amide yield, since it enabled the effective removal of the inhibiting methanol from the reaction mixture.
A catalyst system for the formation of amides by reaction of carboxylic acids with blocked isocyanates
Gertzmann,Gürtler
, p. 6659 - 6662 (2007/10/03)
A catalyst for the reaction of blocked isocyanates (blocking agent diisopropylamine and dimethyl pyrazole) and carboxylic acids was identified. Magnesium and in some instances calcium salts proved to be highly active as catalyst. This reaction gives amides in quantitative yield and excellent selectivity and is suitable for coating and general chemical purposes.
