- Enantioselective Reductive Cyanation and Phosphonylation of Secondary Amides by Iridium and Chiral Thiourea Sequential Catalysis
-
The combination of transition-metal catalysis and organocatalysis increasingly offers chemists opportunities to realize diverse unprecedented chemical transformations. By combining iridium with chiral thiourea catalysis, direct enantioselective reductive cyanation and phosphonylation of secondary amides have been accomplished for the first time for the synthesis of enantioenriched chiral α-aminonitriles and α-aminophosphonates. The protocol is highly efficient and enantioselective, providing a novel route to the synthesis of optically active α-functionalized amines from the simple, readily available feedstocks. In addition, the reactions are scalable and the thiourea catalyst can be recycled and reused.
- Chen, Dong-Huang,Sun, Wei-Ting,Zhu, Cheng-Jie,Lu, Guang-Sheng,Wu, Dong-Ping,Wang, Ai-E,Huang, Pei-Qiang
-
supporting information
p. 8827 - 8831
(2021/03/16)
-
- A process for preparing N - alkyl amide method (by machine translation)
-
The invention discloses a method for preparing N - alkyl amide of the method. In the reaction container, joins the nitrile, oxime, transition metal catalyst iridium complex [Cp * IrCl2 ]2 , Toluene; the reaction mixture in 100 °C reaction under 6 hours, cooling to room temperature; then the alcohol and alkali compound is added, the reaction mixture in the 130 °C react again under 12 hours later, then through the column separation, to obtain the target compound. The invention from the fully commercialized nitrile, proceed wowo and mellow, in the participation of transition metal iridium catalyst, to directly obtain N - alkyl amide, the reaction exhibits three significant advantages: 1) the use of the commercialization of the starting material; 2) low catalyst load; 3) is environment-friendly and easy to control. Therefore, the reaction in accordance with the requirement of green chemistry, has broad prospects of development. (by machine translation)
- -
-
Paragraph 0141; 0142; 0143; 0144; 0145
(2017/08/19)
-
- Method for synthesizing N-alkylamide
-
The invention discloses a method for synthesizing N-alkylamide. In a reaction container, adding nitrile, a complex of a transition-metal catalyst gold, a solvent tetrahydrofuran and H2O; reacting a reaction mixture for several hours at the temperature of 130-140 DEG C, cooling the reaction mixture to room temperature, performing vacuum pressure reduction to remove the solvent; adding a compound alcohol, alkali, the complex of a transition-metal catalyst iridium, a solvent toluene, reacting the reaction mixture for several hours at the temperature of 130 DEG C, through column separation, obtaining a target compound. According to the invention, with participation of the transition-metal catalyst, commercial nitrile is hydrolyzed to generate an amide intermediate, and then is subjected to an alkylation reaction with alcohol to obtain N-alkylamide. The reaction has three obvious advantages: 1) the commercial nitrile and alcohol which is almost nontoxic are taken as initial raw materials; 2) only water is generated as a by-product in the reaction, so that the reaction has no harm on environment; and 3) reaction atom economy is high. The reaction accords with green chemistry requirement, and has wide development prospect.
- -
-
-
- Combination of gold and iridium catalysts for the synthesis of N-alkylated amides from nitriles and alcohols
-
An alternative and efficient approach for the synthesis of N-alkylated amides from nitriles and alcohols was proposed and accomplished. By the combination of [(IPr)Au(NTf2)] (IPr = 1,3-bis(diisopropylphenyl)imidazol-2-ylidene) and [CpIrCl2]2 (Cp = η5-pentamethylcyclopentadienyl), a series of nitriles were first hydrated to give amides, in which the resulting amides were further N-alkylated with a variety of alcohols as alkylating agents to afford N-alkylated amides with good to excellent yields. Compared with previous methods for the synthesis of N-alkylated amides from nitriles and alcohols as starting materials, this protocol could be accomplished with high atom economy under more environmentally benign conditions.
- Li, Feng,Ma, Juan,Lu, Lei,Bao, Xiaofeng,Tang, Wanying
-
p. 1953 - 1960
(2015/04/27)
-
- Ce(III) immobilised on aminated epichlorohydrin-activated agarose matrix - "green" and efficient catalyst for transamidation of carboxamides
-
The present study reports the preparation and characterisation of Ce(III) immobilised on an aminated epichlorohydrin-activated agarose matrix (CAEA) as a "green" catalyst. The catalyst was synthesised by the reaction of the epichlorohydrin-activated agarose matrix with ammonia solution, which was then treated with Ce(NO3)3 · 6H2O. The catalyst (CAEA) was characterised by FT-IR, far IR, CHN, XRD, TGA, and ICP techniques. CAEA is shown to be an effective and reusable heterogeneous catalyst for the transamidation of carboxamides with amines under solventfree conditions. The catalyst was successfully applied to the synthesis of a wide range of aromatic and aliphatic amides. High efficiency, mild reaction conditions, easy work-up, simple separation and also reusability are important advantages of this catalyst.
- Zarei, Zeinab,Akhlaghinia, Batool
-
p. 1421 - 1437
(2015/09/15)
-
- A One-Pot, fast, and efficient amidation of carboxylic acids, α-amino acids and sulfonic acids using pph3/n-chlorobenzotriazole system
-
Triphenylphosphine (PPh3)/N-chlorobenzotriazole (NCBT), and amine (primary and secondary aliphatic amines and also substituted anilines) in CH2Cl2 efficiently converted carboxylic acids, α-amino acids, and sulfonic acids to the corresponding amides and sulfonamides at room temperature. Good to excellent yields, inexpensive, and fast reaction conditions are the important features of this procedure.
- Rouhi-Saadabad, Hamed,Akhlaghinia, Batool
-
p. 1703 - 1714
(2015/09/15)
-
- A novel nickel-catalyzed synthesis of thioesters, esters and amides from aryl iodides in the presence of chromium hexacarbonyl
-
This study describes our findings on a novel and cheap NiCl2 catalytic system under ligand-free conditions for the efficient thiocarbonylation, alkoxycarbonylation and amidocarbonylation reactions of aryl iodides in the presence of Cr(CO)6 as the solid source of carbon monoxide under air. A variety of aryl iodides tolerated the reaction conditions and structurally different thiols, alcohols and amines were used efficiently. The corresponding thioesters, esters and amides were obtained in good to excellent yield at atmospheric pressure under mild reaction conditions.
- Iranpoor, Nasser,Firouzabadi, Habib,Etemadi-Davan, Elham,Nematollahi, Arash,Firouzi, Hamid Reza
-
p. 6445 - 6452
(2015/08/11)
-
- The direct synthesis of N-alkylated amides via a tandem hydration/N-alkylation reaction from nitriles, aldoximes and alcohols
-
A novel strategy for the direct synthesis of N-alkylated amides from nitriles, aldoximes and alcohols was proposed and accomplished in the presence of a Cp*Ir complex. This journal is the Partner Organisations 2014.
- Wang, Nana,Zou, Xiaoyuan,Ma, Juan,Li, Feng
-
p. 8303 - 8305
(2014/07/22)
-