138883-38-2Relevant academic research and scientific papers
Alkylation of Rink's amide linker on polystyrene resin: A reductive amination approach to modified amine-linkers for the solid phase synthesis of N-substituted amide derivatives
Brown, Edward G.,Nuss, John M.
, p. 8457 - 8460 (1997)
Reductive amination of aldehydes and ketones using sodium cyanoborohydride and Rink's 4-(2',4'-dimethoxyphenyl-aminomethyl)-phenoxymethyl-linked polystyrene resin [Rink's amine linker on copoly-(styrene-1%-divinylbenzene)]1 2 affords high yields of linker-bound, N-alkyl amines with excellent chemical selectivity. Subsequent coupling with acid derivatives gave derivatized N-substituted amides in excellent yields after cleavage from the solid-support.
Acetonitrile and benzonitrile as versatile amino sources in copper-catalyzed mild electrochemical C-H amidation reactions
Budnikova, Yulia,Kononov, Alexander,Rizvanov, Ildar,Strekalova, Sofia
, p. 37540 - 37543 (2021/12/07)
A mild, efficient electrochemical approach to the site-selective direct C-H amidation of benzene and its derivatives with acetonitrile and benzonitrile has been developed. It has been shown that joint electrochemical oxidation of various arenes in the presence of a copper salt as a catalyst and nitriles leads to the formation of N-phenylacetamide from benzene and N-benzylacetamides from benzyl derivatives (up to 78% yield). A favorable feature of the process is mild conditions (room temperature, ambient pressure, no strong oxidants) that meet the criteria of green chemistry.
UV-Light-Induced N-Acylation of Amines with α-Diketones
Xu, Zhihui,Yang, Tianbao,Tang, Niu,Ou, Yifeng,Yin, Shuang-Feng,Kambe, Nobuaki,Qiu, Renhua
supporting information, p. 5329 - 5333 (2021/07/21)
Herein, we develop a mild method for N-acylation of primary and secondary amines with α-diketones induced by ultraviolet (UV) light. Forty-six examples with various functional groups are explored at room temperature with irradiation by three 26 W UV lamps (350-380 nm). The yield reaches 97%. The gram scale experiment product yield is 76%. Moreover, this system can be applied to the synthesis of several amino acid derivatives. Mechanistic studies show that benzoin is generated in situ from benzil under UV irradiation.
The synthesis and structure of pyridine-oxadiazole iridium complexes and catalytic applications: Non-coordinating-anion-tuned selective C–N bond formation
Yao, Wei,Zhang, Yilin,Zhu, Haiyan,Ge, Chenyang,Wang, Dawei
, p. 701 - 705 (2019/09/30)
Several novel pyridine-oxadiazole iridium complexes were synthesized and characterized through X-ray crystallography. The designed iridium complexes revealed surprisingly high catalytic activity in C–N bondformation of amides and benzyl alcohols with the assistance of non-coordinating anions. In an attempt to achieve borrowing hydrogen reactions of amides with benzyl alcohols, N,N'-(phenylmethylene)dibenzamide products were unexpectedly isolated under non-coordinating anion conditions, whereas N-benzylbenzamide products were achieved in the absence of non-coordinating anions. The mechanism explorations excluded the possibility of “silver effect” (silver-assisted or bimetallic catalysis) and revealed that the reactivity of iridium catalyst was varied by non-coordinating anions. This work provided a convenient and useful methodology that allowed the iridium complex to be a chemoselective catalyst and demonstrated the first example of non-coordinating-anion-tuned selective C–N bond formation
A convenient synthesis of 2-alkyl-3-aryl-2,3-dihydro-1H-isoindol-1-ones by the reaction of N-alkyl-N-[(2-bromophenyl)methyl]benzamides with butyllithium
Kobayashi, Kazuhiro,Chikazawa, Yuuki
, p. 5100 - 5105 (2016/07/25)
An unprecedented and convenient synthetic approach to 2,3-dihydro-1H-isoindol-1-one (isoindolinone) derivatives has been developed. The key and final step of the method is the reaction of N-alkyl-N-(o-bromobenzyl)benzamides with butyllithium in THF at ?78
C-N Coupling of Amides with Alcohols Catalyzed by N-Heterocyclic Carbene-Phosphine Iridium Complexes
Kerdphon, Sutthichat,Quan, Xu,Parihar, Vijay Singh,Andersson, Pher G.
, p. 11529 - 11537 (2015/12/04)
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.
Copper(I)-Catalyzed Reductive Cross-Coupling of N-Tosylhydrazones with Amides: A Straightforward Method for the Construction of C(sp3)- N Amide Bonds from Aldehydes
Xu, Peng,Han, Fu-She,Wang, Yan-Hua
supporting information, p. 3441 - 3446 (2016/01/25)
A method for the one-pot synthesis of substituted amides from aldehydes and amides is presented. Namely, condensation of aldehydes with N-tosylhydrazide generated the N-tosylhydrazones which were then reductively cross-coupled in situ with primary or secondary amides in the presence of a copper catalyst to afford secondary or tertiary amides, respectively. The reaction proceeded efficiently for a wide range of aldehydes and amides under the optimized conditions, i.e., 10 mol% of tetrakis(acetonitrile)copper(I) tetrafluoroborate [Cu(CH3CN)4BF4], 1 mol% of tetra-n-butylammonium iodide [(n-Bu)4NI], and sodium hydroxide [NaOH] as base in tetrahydrofuran (THF) at 80 C. As a result, the method provides a straightforward route for the synthesis of substituted amides from readily available aldehydes via a transition metal-catalyzed C(sp3)- N amide bond forming reaction.
Facile conversion of thioamides into the corresponding amides in the presence of tetrabutylammonium bromide
Inamoto, Kiyofumi,Shiraishi, Mitsugu,Hiroya, Kou,Doi, Takayuki
experimental part, p. 3087 - 3090 (2010/10/21)
Desulfurization of thioamides was accomplished using a semicatalytic amount of Bu4NBr. The corresponding amides were obtained in high yields, with good functional group compatibility. Georg Thieme Verlag Stuttgart - New York.
An Efficient General Route to Furo-, Pyrido- and Thieno-benzazepines via Pd0 Catalysed Cross Coupling Reactions and Nitrile Ylide Cyclisations
Finch, Harry,Reece, Donald H.,Sharp, John T.
, p. 1193 - 1204 (2007/10/02)
The cyclisation of diene-conjugated nitrile ylides of the general type 1, in which the conjugated system consists of a benzene ring and a five- or a six-membered heterocyclic ring, provides an effective route to fully unsaturated heterocyclobenzazepines.The combination of this cyclisation with a direct route to the nitrile ylide precursors via Pd0 catalysed cross-coupling gives an efficient general synthetic route to these systems from readily available starting materials.
Oxidation during reductive cyclisations using Bu3SnH
Bowman, W. Russell,Heaney, Harry,Jordan, Benjamin M.
, p. 10119 - 10128 (2007/10/02)
Reductive cyclisations using Bu3SnH include an "oxidation" step if the removal of an acidic proton from the intermediate cyclised radical, by Bu3SnH acting as a base, is favourable. A "pseudo" SRN1 mechanism is proposed.
