57409-26-4Relevant academic research and scientific papers
Homoleptic Bis(trimethylsilyl)amides of Yttrium Complexes Catalyzed Hydroboration Reduction of Amides to Amines
Ye, Pengqing,Shao, Yinlin,Ye, Xuanzeng,Zhang, Fangjun,Li, Renhao,Sun, Jiani,Xu, Beihang,Chen, Jiuxi
supporting information, p. 1306 - 1310 (2020/02/22)
Homoleptic lanthanide complex Y[N(TMS)2]3 is an efficient homogeneous catalyst for the hydroboration reduction of secondary amides and tertiary amides to corresponding amines. A series of amides containing different functional groups such as cyano, nitro, and vinyl groups were found to be well-tolerated. This transformation has also been nicely applied to the synthesis of indoles and piribedil. Detailed isotopic labeling experiments, control experiments, and kinetic studies provided cumulative evidence to elucidate the reaction mechanism.
Straightforward α-Amino Nitrile Synthesis Through Mo(CO)6-Catalyzed Reductive Functionalization of Carboxamides
Trillo, Paz,Slagbrand, Tove,Adolfsson, Hans
supporting information, p. 12347 - 12351 (2018/09/10)
The selective reduction of amides into an intermediate hemiaminal catalyzed by Mo(CO)6 together with the inexpensive and easy to handle TMDS (1,1,3,3-tetramethyldisiloxane) as reducing agent, followed by subsequent trapping of the hemiaminal with a cyanide source, allows for the straightforward synthesis of α-amino nitriles. The methodology presented here, displays high levels of chemoselectivity allowing for the reduction of amides in the presence of functional groups such as ketones, imines, aldehydes, and acids, which affords a simple route for the synthesis of α-amino nitriles with a broad scope of functionalities in high yields. Furthermore, the applicability of this methodology is demonstrated by scale up experiments and by derivatization of the target compounds into synthetically interesting products. The selective cyanation is successfully applied in late stage functionalizations of amide containing drugs and prolinol derivatives.
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.
Dioxygen-promoted Pd-catalyzed aminocarbonylation of organoboronic acids with amines and CO: A direct approach to tertiary amides
Ren, Long,Li, Xinwei,Jiao, Ning
supporting information, p. 5852 - 5855 (2016/11/29)
A direct approach from organoboronic acids and amines to tertiary amides via Pd-catalyzed aerobic aminocarbonylation has been developed. The presence of O2 significantly promotes the efficiency of this transformation. This method uses commercially available organoboronic acids and cheap CO and O2 (1 atm), which renders amides an easy synthesis with broad substrate scope and high functional group tolerance.
Iron-catalyzed direct synthesis of amides from methylarenes
Srinivas Kotha, Surya,Badigenchala, Sindhura,Sekar, Govindasamy
, p. 1437 - 1445 (2015/05/19)
An efficient, green and first catalytic process has been developed for the direct synthesis of amides from readily available petroleum by-products (methylarenes) and amines using an iron catalyst. In this new catalytic reaction, the methyl group of the me
Radical-Induced Metal and Solvent-Free Cross-Coupling Using TBAI-TBHP: Oxidative Amidation of Aldehydes and Alcohols with N-Chloramines via C-H Activation
Achar, Tapas Kumar,Mal, Prasenjit
, p. 666 - 672 (2015/08/19)
A solvent-free cross-coupling method for oxidative amidation of aldehydes and alcohols via a metal-free radial pathway has been demonstrated. The proposed methodology uses the TBAI-TBHP combination which efficiently induces metal-free C-H activation of aldehydes under neat conditions at 50 °C or ball-milling conditions at room temperature.
Iodine-catalyzed efficient amide formation from aldehydes and amines
Wang, Peng,Xia, Jiaxuan,Gu, Yueqing
supporting information, p. 7120 - 7123 (2015/12/01)
An efficient iodine-catalyzed radical oxidative amidation of aldehydes with amines has been developed. This methodology was employed to prepare amides in good to excellent yields with the advantages of wide functional group tolerance and operational simplicity.
Efficient metal-free hydrosilylation of tertiary, secondary and primary amides to amines
Blondiaux, Enguerrand,Cantat, Thibault
supporting information, p. 9349 - 9352 (2014/08/05)
Hydrosilylation of secondary and tertiary amides to amines is described using catalytic amounts of B(C6F5)3. The organic catalyst enables the reduction of amides with cost-efficient, non-toxic and air stable PMHS and TMDS hydrosilanes. The methodology was successfully extended to the more challenging reduction of primary amides.
A novel Pd-catalyzed N-dealkylative carbonylation of tertiary amines for the preparation of amides
Fang, Tao,Gao, Xu-Hong,Tang, Ri-Yuan,Zhang, Xing-Guo,Deng, Chen-Liang
supporting information, p. 14775 - 14777 (2014/12/11)
A novel and convenient protocol for the formation of amides via palladium-catalyzed N-dealkylative carbonylation of alkyl tertiary amines has been developed. In the presence of PdCl2(PhCN)2, CuO, PhCN and CO, a range of substituents on both aryl iodides and alkyl tertiary amines were compatible with the reaction to afford a series of N,N-disubstituted amides in moderate to excellent yields. This journal is
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.
