7504-58-7Relevant academic research and scientific papers
Accelerating reactions with microreactors at elevated temperatures and pressures: Profiling aminocarbonylation reactions
Murphy, Edward R.,Martinelli, Joseph R.,Zaborenko, Nikolay,Buchwald, Stephen L.,Jensen, Klavs F.
, p. 1734 - 1737 (2007)
Squeeze play: Pressurized microreactor systems greatly expand the range of reaction conditions and accelerate gas-liquid mass transfer. Heck aminocarbonylation reactions (see scheme) exemplify the potential for the quick and safe scanning of reagents and
NaI-mediated oxidative amidation of benzyl alcohols/aromatic aldehydes to benzamides via electrochemical reaction
Rerkrachaneekorn, Tanawat,Tankam, Theeranon,Sukwattanasinitt, Mongkol,Wacharasindhu, Sumrit
supporting information, (2021/04/15)
In this research, we have developed a mild electrochemical process for oxidative amidation of benzyl alcohols/aromatic aldehydes with cyclic amines into the corresponding benzamides. This electroorganic synthetic method proceeds using NaI as a redox mediator under ambient temperature in undivided cell, providing more than 25 examples of amide products in moderate to good yields. The benefits of this reaction include one-pot synthesis, open air condition, proceed in aqueous media and no requirement of external conducting salt, base and oxidant.
Direct Amidation of Esters by Ball Milling**
Barreteau, Fabien,Battilocchio, Claudio,Browne, Duncan L.,Godineau, Edouard,Leitch, Jamie A.,Nicholson, William I.,Payne, Riley,Priestley, Ian
supporting information, p. 21868 - 21874 (2021/09/02)
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.
Organophotoredox-Mediated Amide Synthesis by Coupling Alcohol and Amine through Aerobic Oxidation of Alcohol
Samanta, Samya,Shah, Sk. Sheriff,Shee, Maniklal,Singh, Amit Kumar,Singh, N. D. Pradeep,Venkatesh, Yarra
supporting information, (2020/03/05)
The combination of an organic photocatalyst [4CzIPN (1,2,3,5-tetrakis(carbazol-9-yl)-4,6 dicyanobenzene) or 5MeOCzBN (2,3,4,5,6-pentakis(3,6-dimethoxy-9 H-carbazol-9-yl)benzonitrile)], quinuclidine, and tetra-n-butylammonium phosphate (hydrogen-bonding catalyst) was employed for amide bond formations. The hydrogen-bonded OH group activated the adjacent C?H bond of alcohols towards hydrogen atom transfer (HAT) by a radical species. The quinuclidinium radical cation, generated through single-electron oxidation of quinuclidine by the photocatalyst, employed to abstract a hydrogen atom from the α-C?H bond of alcohols selectively due to a polarity effect-produced α-hydroxyalkyl radical, which subsequently converted to the corresponding aldehyde under aerobic conditions. Then the coupling of the aldehyde and an amine formed a hemiaminal intermediate that upon photocatalytic oxidation produced the amide.
Double carbonylation of iodoarenes in the presence of a pyridinium SILP-Pd catalyst
Nagy, Enik?,Nagy, Petra,Papp, Máté,Skoda-F?ldes, Rita,Urbán, Béla
, (2020/04/28)
The efficiency of a palladium catalyst, immobilised on a supported ionic liquid phase (SILP) with adsorbed 1-butyl-4-methylpyridinium chloride, was investigated in aminocarbonylation reactions. Double carbonylation was found to be the main reaction using different iodoarenes and aliphatic amines as substrates. Application of aniline derivatives as nucleophiles led to the exclusive formation of substituted benzamides. The stabilisation effect of the adsorbed pyridinium ionic liquid was compared to that of imidazolium and phosphonium derivatives. It was proved that the pyridinium SILP-palladium catalyst could be reused in at least 10 cycles. Recyclability was tested in five successive runs for all of the substrates.
Supramolecular Pd(II) complex of DPPF and dithiolate: An efficient catalyst for amino and phenoxycarbonylation using Co2(CO)8 as sustainable C1 source
Gaikwad, Vinayak V.,Mane, Pravin A.,Dey, Sandip,Patel, Divya,Bhanage, Bhalchandra M.
, (2019/11/28)
Highly active, efficient and robust “dppf ligated tetranuclear palladium dithiolate complex” was synthesized and applied as a catalyst for chemical fixation of carbon monoxide for the synthesis value added chemicals such as tertiary amide and aromatic esters. The synthesized catalyst was characterized using different analytical techniques such as elemental analysis, 1H and 31P NMR spectroscopy. The use of Co2(CO)8 as a cheap, less toxic and low melting solid surrogate are additional advantages over the current protocol. The catalyst showed superior activity towards the Amino (10?3 mol % catalyst) and Phenoxycarbonylation (10-2 mol % catalyst) and high TON (104 to 103) and TOF (103 to 102 h-1). The Betol and Lintrin (active drug molecules) were synthesized under an optimized reaction condition. The scalability of the current protocol has been demonstrated up-to the gram level.
Synthesis method of amide compound
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Paragraph 0096; 0097, (2020/09/09)
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.
Cobalt-catalyzed aminocarbonylation of (hetero)aryl halides promoted by visible light
Alexanian, Erik J.,Veatch, Alexander M.
, p. 7210 - 7213 (2020/07/23)
The catalytic aminocarbonylation of (hetero)aryl halides is widely applied in the synthesis of amides but relies heavily on the use of precious metal catalysis. Herein, we report an aminocarbonylation of (hetero)aryl halides using a simple cobalt catalyst under visible light irradiation. The reaction extends to the use of (hetero)aryl chlorides and is successful with a broad range of amine nucleophiles. Mechanistic investigations are consistent with a reaction proceeding via intermolecular charge transfer involving a donor-acceptor complex of the substrate and cobaltate catalyst.
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.
Quinolin-8-yl Formate: A New Option for Small-Scale Carbonylation Reactions in Microwave Reactors
Maddocks, Christopher J.,Aathimanikandan, Sivakumar V.,Richardson, Jeffery,Ruble, J. Craig
, p. 1608 - 1612 (2020/09/09)
A convenient procedure for conducting small-scale carbonylations of aryl or benzyl halides in a microwave reactor by using quinolin-8-yl formate is described. The resulting 8-acyloxyquinolines were shown to be more reactive than phenyl esters in acyl-tran
