33388-67-9Relevant academic research and scientific papers
METHODS OF CONTROLLING CROP PESTS USING AROMATIC AMIDE INSECT REPELLENTS, METHODS OF MAKING AROMATIC AMIDE INSECT REPELLENTS, AND NOVEL AROMATIC AMIDE INSECT REPELLENTS
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Paragraph 0068-0069, (2022/03/18)
Methods of protecting fruit crops from flying insect pests and of repelling flying insects using aromatic amide compounds are disclosed. The methods apply the compounds to various surfaces, such as the fruit crops, the ground or structures adjacent to the fruit crops, or an object, article, human skin or animal. The compounds have the formula RxC6Hy—C(═O)—N(Cy), where RxC6Hy is a substituted phenyl group, each R group is independently C1-C6 alkyl, substituted C1-C4 alkyl, (substituted) C6-C10 aryl, C1-C4 alkoxy, C6-C10 aryloxy, halogen, nitro, cyano, cyanate, isocyanate, nitroso, C1-C4 alkylthio, phenylthio, (halogen-substituted) C1-C4 alkylsulfonyl, phenylsulfonyl, tolylsulfonyl, amino, mono- or di-C1-C4 alkylamino, diphenylamino, di-C1-C4 alkylamido, formyl, C2-C7 acyl, or C1-C6 alkoxycarbonyl; x is an integer of 1 to 5; x+y=5; Cy is a C2-C8 (substituted) alkadiyl, a C4-C6 (substituted) alkenediyl, or a (substituted) diyl of the formula —(CH2CH2)—O—(CH2CH2)—, —(CH2CH2)—NR′—(CH2CH2)— or —(CH2CH2)—S—(CH2CH2)— that, along with the amide N atom, forms a non-aromatic cyclic group; and R′ is C1-C6 alkyl, substituted C1-C4 alkyl, (substituted) C6-C10 aryl, or (substituted) benzyl.
Direct Synthesis of Enamides via Electrophilic Activation of Amides
Berger, Martin,Kaiser, Daniel,Maulide, Nuno,Spie?, Philipp
supporting information, p. 10524 - 10529 (2021/07/28)
A novel, one-step N-dehydrogenation of amides to enamides is reported. This reaction employs the unlikely combination of LiHMDS and triflic anhydride, which serves as both the electrophilic activator and the oxidant, and is characterized by its simple setup and broad substrate scope. The synthetic utility of the formed enamides was readily demonstrated in a range of downstream transformations.
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.
Visible-Light-Mediated Efficient Metal-Free Catalyst for α-Oxygenation of Tertiary Amines to Amides
Zhang, Yu,Riemer, Daniel,Schilling, Waldemar,Kollmann, Jiri,Das, Shoubhik
, p. 6659 - 6664 (2018/06/25)
A metal-free system has been discovered for the efficient α-oxygenation of tertiary amines to the corresponding amides using oxygen as an oxidant. This visible-light-mediated oxygenation reaction exhibited excellent substrates scope under mild reaction conditions and generated water as the only byproduct. The synthetic utility of this approach has been demonstrated by applying onto drug molecules. At the end, detailed mechanistic reactions clearly showed the role of oxygen and the photocatalyst.
1,1,2,2-Tetrahydroperoxy-1,2-Diphenylethane: An efficient and high oxygen content oxidant in various oxidative reactions
Khosravi, Kaveh,Naserifar, Shirin
supporting information, p. 6584 - 6592 (2018/10/05)
Several oxidative approaches namely thiocyanation of aromatic compounds, epoxidation of alkenes, amidation of aromatic aldehydes, epoxidation of α β-unsaturated ketones, oxidation of sulfides to sulfoxides and sulfones, bayer-villeger reaction, bromination and iodation of aniline and phenol derivatives oxidative esterification, oxidation of pyridines and oxidation of secondary, allylic and benzyllic alcohols were carried out using 1,1,2,2-Tetrahydroperoxy-1,2-Diphenylethane as the potential solid oxidant which can be stored for several months without any loss in its activity. All of the procedures were accomplished via mild reaction conditions and the products were afforded in high yields and short reaction times.
A Manganese Pre-Catalyst: Mild Reduction of Amides, Ketones, Aldehydes, and Esters
Kelly, Colin M.,McDonald, Robert,Sydora, Orson L.,Stradiotto, Mark,Turculet, Laura
supporting information, p. 15901 - 15904 (2017/12/13)
A new (N-phosphinoamidinate)manganese complex is shown to be a useful pre-catalyst for the hydrosilative reduction of carbonyl compounds, and in most cases at room temperature. The Mn-catalyzed reduction of tertiary amides to tertiary amines, with a useful scope, is demonstrated for the first time by use of this catalyst, and is competitive with the most effective transition-metal catalysts known for such transformations. Ketones, aldehydes, and esters were also successfully reduced under mild conditions by using this new Mn catalyst.
Palladium-Catalyzed Carbonylative Synthesis of Amides from Aryltriazenes under Additive-Free Conditions
Yin, Zhiping,Wang, Zechao,Wu, Xiao-Feng
supporting information, p. 3992 - 3995 (2017/07/28)
An interesting palladium-catalyzed carbonylative synthesis of amides from aryltriazenes was developed. By using Pd(MeCN2)Cl2 as the catalyst precursor under CO pressure through a N2 extrusion/CO insertion sequence, a broad range of aryltriazenes were transformed into the corresponding amides in good yields with excellent functional group tolerance. Remarkably, no additives such as acids or phosphine ligands were required.
Practical Synthesis of Amides via Copper/ABNO-Catalyzed Aerobic Oxidative Coupling of Alcohols and Amines
Zultanski, Susan L.,Zhao, Jingyi,Stahl, Shannon S.
supporting information, p. 6416 - 6419 (2016/06/09)
A modular Cu/ABNO catalyst system has been identified that enables efficient aerobic oxidative coupling of alcohols and amines to amides. All four permutations of benzylic/aliphatic alcohols and primary/secondary amines are viable in this reaction, enabling broad access to secondary and tertiary amides. The reactions exhibit excellent functional group compatibility and are complete within 30 min-3 h at rt. All components of the catalyst system are commercially available.
Iron-catalysed oxidative amidation of alcohols with amines
Gaspa, Silvia,Porcheddu, Andrea,De Luca, Lidia
supporting information, p. 3803 - 3807 (2013/07/26)
A new iron-catalysed oxidative amidation of differently substituted benzylic alcohols with mono- and di-substituted amines was developed. The Royal Society of Chemistry 2013.
Iron-catalyzed amidation of aldehydes with N-chloroamines
Porcheddu, Andrea,Luca, Lidia De
, p. 2949 - 2953,5 (2012/12/13)
A new direct conversion of aldehydes to amides has been realized, in the presence of iron(III) chloride as a catalyst and using tert-butyl hydroperoxide (TBHP) as an oxidant. Both aliphatic and aromatic aldehydes were successfully reacted with variously mono- and di-substituted N-chloroamines. The methodology has a wide substrate scope, uses cheap and easily available reagents and is characterized by short reaction times. Copyright
