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Rhodium-catalyzed arylation and alkenylation of imines with organostannanes
A rhodium complex catalyzed the addition of aryl- and alkenyl-stannanes to activated aldimines under mild and neutral conditions, affording the corresponding amines in good yields.
Oi, Shuichi,Moro, Mitsutoshi,Fukuhara, Hiroe,Kawanishi, Takanori,Inoue, Yoshio
p. 9259 - 9262
(1999)
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Bird
p. 4091
(1962)
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A mild and efficient method for formation of C-N bond from benzyl alcohols and sulfonamide, carboxamide, 4-nitroanline and azide catalysed by SnCl 4
A mild and efficient method for the formation of C-N bonds is reported with SnCl4 as an inexpensive catalyst. With 10 mol% of SnCl4, the direct substitution reaction of secondary benzyl alcohols with a sulfonamide, a carboxamide, 4-nitroaniline and an azide proceeds well in good to excellent yields at room temperature.
Li, Lingjun,Zhu, Anlian,Yao, Huiwen,Wei, Yujing,Yang, Di,Li, Jianping,Zhang, Guisheng
p. 511 - 513
(2010)
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An expedient, efficient and solvent-free synthesis of T3P-mediated amidation of benzhydrols with poorly reactive N-nucleophiles under MW irradiation
An expedient, efficient, economical, environmentally benign, and solvent free amidation protocol of benzhydrols with less reactive nitrogen nucleophiles assisted by propylphosphonic anhydride (T3P) under microwave irradiation has been developed. The methodology has been deployed for a wide range of heterocycles and electron-withdrawing & electron-donating groups. The protocol resulted in good to excellent yields under the given conditions (26 examples, 68-93% yield).
Cheruku, Srinivas,Manikyanally, Kumara N.,Mantelingu, Kempegowda,Nagarakere, Sandhya C.,Narayana, Yatheesh,Rangappa, Kanchugarakoppal S.,Sunilkumar, Makanahalli P.
p. 4421 - 4426
(2022/03/14)

Method for synthesizing amide compound by taking nitrile and diaryl methane as raw materials
The invention discloses a method for synthesizing an amide compound by taking nitrile and diaryl methane as raw materials, the method comprises the following steps: taking diaryl methane as a reaction raw material, nitrile as a raw material and a solvent, 2, 3-dichloro-5, 6-dinitrile group-1, 4-benzoquinone (DDQ) and tert-butyl nitrite (TBN) as catalysts, acid as an auxiliary agent and oxygen as an oxidizing agent, reacting under the conditions of normal temperature, normal pressure and blue light irradiation, and after the reaction is finished, carrying out separation treatment to obtain the amide compound. According to the method, the problem of metal residues in the product can be solved, oxygen is used as a terminal oxidizing agent, the method is environmentally friendly, and energy can be saved.
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Paragraph 0030-0040

(2022/01/20)

Metal-free transamidation of benzoylpyrrolidin-2-one and amines under aqueous conditions
N-Acyl lactam amides, such as benzoylpyrrolidin-2-one, benzoylpiperidin-2-one, and benzoylazepan-2-one reacted with amines in the presence of DTBP and TBAI to afford the transamidated products in good yields. The reactions were conducted under aqueous conditions and good functional group tolerance was achieved. Both aliphatic and aromatic primary amines displayed good activity under metal-free conditions. A radical reaction pathway is proposed.
Joseph, Devaneyan,Lee, Sunwoo,Park, Myeong Seong
supporting information
p. 6227 - 6232
(2021/07/28)

Interweaving Visible-Light and Iron Catalysis for Nitrene Formation and Transformation with Dioxazolones
Herein, visible-light-driven iron-catalyzed nitrene transfer reactions with dioxazolones for intermolecular C(sp3)-N, N=S, and N=P bond formation are described. These reactions occur with exogenous-ligand-free process and feature satisfactory to excellent yields (up to 99 %), an ample substrate scope (109 examples) under mild reaction conditions. In contrast to intramolecular C?H amidations strategies, an intermolecular regioselective C?H amidation via visible-light-induced nitrene transfer reactions is devised. Mechanistic studies indicate that the reaction proceeds via a radical pathway. Computational studies show that the decarboxylation of dioxazolone depends on the conversion of ground sextet state dioxazolone-bounding iron species to quartet spin state via visible-light irradiation.
Tang, Jing-Jing,Yu, Xiaoqiang,Wang, Yi,Yamamoto, Yoshinori,Bao, Ming
p. 16426 - 16435
(2021/05/13)

Preparation method of photocatalytic N-alkylamide compound
The invention belongs to the technical field of organic synthesis, and provides a preparation method of an N-alkylamide compound. According to the method, a dioxazolone compound and an alkane derivative are used as raw materials, a manganese catalyst and an additive react for 12-24 hours in an organic solvent under a mild condition under photocatalysis, and the product is converted into an N-alkylamide compound. The method has the beneficial effects that the raw materials are cheap and easy to obtain, the conditions are mild, the method is environment-friendly, the possibility of industrialization is realized, and the yield of the N-alkylamide compound is high; the N-alkylamide compound can be further functionalized to obtain various compounds, and is applied to development and research of natural products, functional materials and fine chemicals.
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Paragraph 0049-0052

(2021/04/17)

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)

Dehydrogenative amide synthesis from alcohols and amines utilizing N-heterocyclic carbene-based ruthenium complexes as efficient catalysts: The influence of catalyst loadings, ancillary and added ligands
The metal-catalyzed dehydrogenative coupling of alcohols and amines to access amides has been recognized as an atom-economic and environmental-friendly process. Apart from the formation of the amide products, three other kinds of compounds (esters, imines and amines) may also be produced. Therefore, it is of vital importance to investigate product distribution in this transformation. Herein, N-heterocyclic carbene-based Ru (NHC/Ru) complexes [Ru-1]-[Ru-5] with different ancillary ligands were prepared and characterized. Based on these complexes, we selected condition A (without an added NHC precursor) and condition B (with an added NHC precursor) to comprehensively explore the selectivity and yield of the desired amides. After careful evaluation of various parameters, the Ru loadings, added NHC precursors and the electronic/steric properties of ancillary NHC ligands were found to have considerable influence on this catalytic process.
Wang, Wan-Qiang,Wang, Zhi-Qin,Sang, Wei,Zhang, Rui,Cheng, Hua,Chen, Cheng,Peng, Da-Yong
(2021/01/05)

Chemoselective formation of C–N bond in wet acetonitrile using amberlyst-15(H) as a recyclable catalyst
An economically efficient and environmentally benign protocol for the chemoselective one-pot synthesis of diversely N-substituted amides has been developed in good yield through the reaction of benzylic secondary alcohols as well as aliphatic tertiary alcohols and alkyl/aryl nitriles. Commercially available Amberlyst-15(H) has been utilized at 80 °C as an air-stable and reusable heterogeneous inexpensive solid acid catalyst without any anhydrous and inert environment. The attractive features of the present synthetic protocol are mild reaction conditions, short reaction time, excellent chemoselectivity, high atom economy and tolerance of various sensitive moieties.
Nandy, Sneha,Das, Asit Kumar,Bhar, Sanjay
supporting information
p. 3326 - 3336
(2020/08/13)

Nickel/briphos-catalyzed transamidation of unactivated tertiary amides
The transamidation of tertiary amides was achieved via nickel catalysis in combination with briphos ligands. N-Methyl-N-phenylbenzamide derivatives reacted with primary amines in the presence of NiCl2/briphos L4 to provide the transamidated products in moderate to good yields. Primary aromatic amines delivered higher product yields than aliphatic amines.
Kim, Hyunwoo,Lee, Sunwoo,Shin, Taeil,Yang, Dahyeon
supporting information
p. 6053 - 6057
(2020/10/27)

Benzyl C–O and C–N Bond Construction via C–C Bond Dissociation of Oxime Ester under Visible Light Irradiation
A photoredox benzyl activation was developed via formidable C(sp3)–C(sp3) bond dissociation of 1-aryl acetone oxime esters, which were easily prepared from benzyl ketones. Further coupling with O- and N- nucleophiles successfully forged important benzyl ether and amines derivatives in one pot. In this process, different substitutions on oxime esters were found compatible and various primary and secondary alcohols and amines, as well as amides showed good performance as nucleophiles. Mechanistic studies by control experiments, electrochemical measurements and in-situ NMR spectra proposed a N–O bond interruption/C–C bond fragmentation/oxidation sequence to provide the key cation intermediate for the next electrophilic SN process. The features of mild condition, short reaction time and broad substrate scope made this new strategy much promising in the transformation of benzyl compounds, which might be valuable in last-stage functionalizations.
Fan, Xiuwei,Lei, Tao,Liu, Zan,Yang, Xiu-Long,Cheng, Yuan-Yuan,Liang, Ge,Chen, Bin,Tung, Chen-Ho,Wu, Li-Zhu
p. 1551 - 1558
(2019/09/09)

An efficient metal-free oxidative esterification and amination of benzyl C-H bond
An esterification and amination of benzylic C-H bonds was developed by using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) under metal- and iodide-free conditions. Both carboxylic acids and amines could be used as ideal coupling partners for the oxidati
Liu, Saiwen,Chen, Ru,He, Guowen,Zhang, Jin
(2020/04/09)

Innovative approach for the synthesis of N-substituted amides from nitriles and alcohols using propylphosphonic anhydride (T3P) under solvent-free conditions
Novel and convenient methodology for the construction of N-substituted amide derivatives have been developed from nitriles and alcohols using propylphosphonic anhydride (T3P). This methodology is an alternate approach to the synthesis of amides via Ritter reaction, which is one of the classical methods for the synthesis of N-substituted amides from nitriles and alcohols. In this approach, first T3P activates the alcohol which is then attacked by nitrile to form N-substituted amides. This methodology can also apply for the synthesis of benzhydryl ether. This developed protocol is one of the novel applications of T3P.
Chaithra, Nagaraju,Mantelingu, Kempegowda,Rangappa, Kanchugarakoppal S.,Rangappa, Shobith,Sandhya, Nagarakere C.,Swarup, Hassan A.
p. 2106 - 2116
(2020/03/13)

Environmentally Benign Ritter Reaction Using Bismuth Salts as a Catalyst
We developed an environmentally benign Ritter reaction of alcohols with nitriles using a commercially available bismuth salt as a less harmful catalyst. The detailed reaction profiles revealed that consumption of the ether by-product as the reaction proceeded was the key for optimizing this reaction, and the yield of the target amide was improved by adding a small amount of water. This finding clearly reveals the significance of using a bismuth salt as the catalyst, as it is not deactivated in the presence of water. This catalyst system has a broad substrate scope, and even with 1 mol-% of the catalyst, the reaction progresses smoothly. It is also possible to react stoichiometric amounts of nitriles and alcohols, thus reducing the amount of organic solvent required for the reaction. Furthermore, as the inexpensive bismuth catalyst can be easily removed using aqueous hydrochloric acid, a purification process that only required washing and drying without any organic solvents was successfully established.
Ueno, Masaharu,Kusaka, Ryo,Ohmura, Satoshi D.,Miyoshi, Norikazu
supporting information
p. 1796 - 1800
(2019/02/07)

An efficient transformation of methyl ethers and nitriles to amides catalyzed by Iron(III) perchlorate hydrate
An efficient and inexpensive synthesis of N-substituted amides from the reaction of nitriles with methyl ethers catalyzed by Fe(ClO4)3·H2O is described. Fe(ClO4)3·H2O is an economically efficient catalyst for the Ritter Reaction under solvent-free conditions. A range of methyl ethers (benzyl, sec-alkyl and tert-butyl ethers) were reacted with nitriles to provide the corresponding amides in high–excellent yields.
Yin, Guibo,Yan, Bin,Chen, Junqing,Ji, Min
p. 1355 - 1363
(2019/04/30)

Selective and Catalytic Hydrocarboxylation of Enamides and Imines with CO2 to Generate α,α-Disubstituted α-Amino Acids
The first catalytic hydrocarboxylation of enamides and imines with CO2 to generate valuable α,α-disubstituted α-amino acids is reported. Notably, excellent chemo- and regio-selectivity are achieved, significantly different from previous reports
Ju, Tao,Fu, Qiang,Ye, Jian-Heng,Zhang, Zhen,Liao, Li-Li,Yan, Si-Shun,Tian, Xing-Yang,Luo, Shu-Ping,Li, Jing,Yu, Da-Gang
supporting information
p. 13897 - 13901
(2018/09/27)

Air-stable Bis(pentamethylcyclopentadienyl) Zirconium Perfluorooctanesulfonate as an Efficient and Recyclable Catalyst for the Synthesis of N-substituted Amides
Bis(pentamethylcyclopentadienyl) zirconium perfluorooctanesulfonate is an air-stable and water-tolerant Lewis acid. This complex exhibited good thermal stability and high solubility in polar organic solvents. The compound showed relatively strong acidity, with an acid strength of 0.8Ho≤3.3, and high catalytic efficiency for the synthesis of N-substituted amides via the reaction of carboxylic acids with amines, the Ritter reaction of nitriles with alcohols, and the amination of alcohols with amides. Moreover, the complex had good reusability. This catalytic system affords a simple and efficient way to synthesize N-substituted amides.
Li, Ningbo,Wang, Lingxiao,Zhang, Liting,Zhao, Wenjie,Qiao, Jie,Xu, Xinhua,Liang, Zhiwu
p. 3532 - 3538
(2018/08/01)

A Pseudodearomatized PN3P?Ni-H Complex as a Ligand and σ-Nucleophilic Catalyst
In contrast to the conventional strategy of modifying the reactivities and selectivities of the transition metal and organocatalysts by varying the steric and electronic properties of organic substituent groups, we hereby demonstrate a novel approach that the sigma (σ) nucleophilicity of the imine arm can be significantly enhanced in a pseudodearomatized PN3P? pincer ligand platform to reach unprecedented N-heterocyclic carbene-like reactivity. Accordingly, the imine arm of the PN3P?Ni-H pincer complex efficiently catalyzes the hydrosilylation of aldehydes, cycloaddition of carbon dioxide (CO2) to epoxides, and serves as a ligand in the Ru-catalyzed dehydrogenative acylation of amines with alcohols.
Li, Huaifeng,Gon?alves, Théo P.,Hu, Jinsong,Zhao, Qianyi,Gong, Dirong,Lai, Zhiping,Wang, Zhixiang,Zheng, Junrong,Huang, Kuo-Wei
p. 14969 - 14977
(2019/01/03)

Nickel/Briphos-Catalyzed Direct Transamidation of Unactivated Secondary Amides Using Trimethylsilyl Chloride
Direct transamidation of secondary amides was developed via nickel catalysis. In the presence of trimethylsilyl chloride and manganese, Ni(diglyme)Cl2 with a Briphos ligand efficiently promoted the transamidation of N-aryl benzamide derivatives with primary amines to afford the corresponding secondary amides in moderate to good yields. Primary amines bearing electron-donating groups gave higher yields of the transamidation products.
Yu, Subeen,Shin, Taeil,Zhang, Maosheng,Xia, Yuanzhi,Kim, Hyunwoo,Lee, Sunwoo
supporting information
p. 7563 - 7566
(2019/01/03)

Fe(ClO 4) 3 ·h 2 O-Catalyzed Ritter Reaction: A Convenient Synthesis of Amides from Esters and Nitriles
An efficient and inexpensive synthesis of N-substituted amides from the Ritter reaction of nitriles with esters catalyzed by Fe(ClO 4) 3 ·H 2 O is described. Fe(ClO 4) 3 ·H 2 O is an economically efficient catalyst for the Ritter reaction under solvent-free conditions. Reactions of a range of esters (benzyl, sec-alkyl, and tert-butyl esters) with nitriles (primary, secondary, tertiary, and aryl nitriles) were performed to provide the corresponding amides in high to excellent yields.
Feng, Chengliang,Yan, Bin,Yin, Guibo,Chen, Junqing,Ji, Min
p. 2257 - 2264
(2018/10/20)

An Atom-Economical Route to Substituted β-Arylethyl Ketones: Phosphomolybdic Acid-Catalyzed Carbohydroxylation of Terminal Alkynes in Organic Carbonate
A highly efficient and atom-economical route for the synthesis of substituted β-arylethyl ketones was developed by using cheap phosphomolybdic acid (H3PMo12O40) as catalyst and non-volatile propylene carbonate (PC) as green solvent via the carbohydroxylation of terminal alkynes with benzylic alcohols under mild conditions. Various functional groups on the benzylic alcohols and terminal alkynes were tolerated, giving the corresponding substituted β-arylethyl ketones as products in good to excellent yields (up to 95%). It is worth noting that a turnover number (TON) of up to 520 was achieved in the protocol. The mechanism investigation showed that PC might stabilize the heteropoly anion and the carbocation intermediate thus facilitating the carbohydroxylation reaction. (Figure presented.).
Yang, Guo-Ping,Zhang, Nan,Ma, Nuan-Nuan,Yu, Bing,Hu, Chang-Wen
p. 926 - 932
(2017/03/27)

Manganese(III) acetate catalyzed oxidative amination of benzylic C(sp3)-H bonds with nitriles
Mn-Catalyzed oxidative amination of benzylic C(sp3)-H bonds with nitriles is disclosed, which enables the synthesis of a broad range of secondary amides in moderate to excellent yields under mild conditions. The interaction between Mn(iii) and DDQ facilitates the oxidation and makes it highly efficient and selective.
Zhang, Yaxing,Dong, Jianyu,Liu, Lixin,Liu, Long,Zhou, Yongbo,Yin, Shuang-Feng
supporting information
p. 2897 - 2901
(2017/04/11)

Method for preparing amide from aryl methane derivative and nitrile
The invention provides a simple and efficient method for directly preparing an amide compound from an aryl methane derivative and nitrile. In the method, manganese triacetate dihydrate is used as a catalyst, and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone(DDQ) is used as an oxidizing agent. The method has the characteristics that raw materials are cheap and easy to obtain, the source of the nitrile is wide, reaction conditions are mild, the applicability is wide and the like. The method solves the problems that ceric ammonium nitrate (CAN) and a fluorine agent which are used by a method for directly synthesizing amide by using aryl methane and nitrile compounds are hard to treat, atomic economy is poor, the source of the nitrile is narrow and the like.
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Paragraph 0047-0049

(2017/05/10)

Selective catalytic Hofmann: N -alkylation of poor nucleophilic amines and amides with catalytic amounts of alkyl halides
Using only catalytic amounts of alkyl halides in the reactions of poor nucleophilic amines/amides and alcohols led to a selective Hofmann N-alkylation reaction catalytic in alkyl halides, providing a practical and efficient method for the practical synthesis of mono- or di-alkylated amines/amides in high selectivities. This new method avoids the use of large amounts of bases, alkyl halides, and solvents, and generates water as the only byproduct. Preliminary mechanistic studies showed that alkyl halides are key intermediates/catalysts regeneratable in the reaction cycle.
Xu, Qing,Xie, Huamei,Zhang, Er-Lei,Ma, Xiantao,Chen, Jianhui,Yu, Xiao-Chun,Li, Huan
supporting information
p. 3940 - 3944
(2016/07/21)

Functional ion liquid method for catalytic synthesis of amine compounds
The invention discloses a method for synthesizing an amine compound catalyzed by functionalized ionic liquid. According to the method, functionalized ionic liquid is used as a catalyst to catalyze N-alkylation of amine and alcohol to synthesize corresponding compound derivatives. Acid functionalized ionic liquid is used as the catalyst to synthesize a series of compounds of amine. The method has the following advantages: a catalytic system is a metal-free system; the usage amount of the catalyst is small, and the catalyst has high catalytic activity, good stability and low corrosivity; operation is simple, and reaction is mild; post-treatment is easy, and the catalyst can be cyclically used.
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Paragraph 0180; 0181; 0182

(2016/10/07)

An efficient and convenient synthesis of N-substituted amides under heterogeneous condition using Al(HSO4)3 via Ritter reaction
An efficient and inexpensive synthesis of N-substituted amides from the reaction of aliphatic and aromatic nitriles with various benzylic alcohols (secondary and tertiary) and tert-butyl alcohol by refluxing nitromethane via the Ritter reaction catalyzed by aluminum hydrogen sulfate [Al(HSO4)3] is described. The catalyst which is an air-stable, cost-effective solid acid could be readily recycled by filtration and reused four times without any significant loss of its activity. [Figure not available: see fulltext.]
Karimian, Elnaz,Akhlaghinia, Batool,Ghodsinia, Sara S.E.
p. 429 - 439
(2016/03/16)

Indium-Triflate-Catalyzed Ritter Reaction in Liquid Sulfur Dioxide
The use of liquid sulfur dioxide as a reaction solvent facilitates the Ritter reaction between alcohols and nitriles. In(OTf)3 was found to be a viable catalyst for this transformation. The newly developed catalytic conditions for the Ritter reaction were successfully applied to the synthesis of various amides, which were formed in good to excellent yields. The catalytic activation of secondary alcohols for Ritter reactions in liquid sulfur dioxide was also found to be effective.
Posevins, Daniels,Suta, Krista,Turks, Maris
supporting information
p. 1414 - 1419
(2016/03/19)

TfOH catalyzed One-Pot Schmidt–Ritter reaction for the synthesis of amides through N-acylimides
A One-Pot tandem Schmidt–Ritter process for the synthesis of amides has been developed using the super acid as catalyst. The in situ generated aryl/aliphatic nitriles from the reaction of aldehydes and sodium azide in the presence of TfOH and AcOH (Schmidt reaction) react with suitable alcohol (Ritter reaction) to give the amides. For the first time we observed that during the Schmidt process N-acylimides were generated along with nitriles, interestingly these N-acylimides also participated in the Ritter reaction.
Singh, Garima,Dada, Ravikrishna,Yaragorla, Srinivasarao
p. 4424 - 4427
(2016/09/13)

Copper-Catalyzed Reductive N-Alkylation of Amides with N-Tosylhydrazones Derived from Ketones
A CuI-catalyzed reductive coupling of ketone-derived N-tosylhydrazones with amides is presented. Under the optimized conditions, an array of N-tosylhydrazones derived from aryl–alkyl and diaryl ketones could couple effectively with a wide variety of (hete
Xu, Peng,Qi, Fu-Ling,Han, Fu-She,Wang, Yan-Hua
p. 2030 - 2034
(2016/07/28)

Practical Synthesis of N -(Diphenylmethyl)- and N -(1-Adamantyl)amides Directly from Aldehydes via a One-Pot Schmidt and Ritter Reaction Sequence
Nonoxidative and noncoupling reaction conditions have been developed for the synthesis of N-(diphenylmethyl)- and N-(1-adamantyl)amide derivatives directly from aldehydes by employing the concept of a Schmidt and Ritter reaction sequence in a one-pot operation. The reagent mixture consisting of sodium azide and HBF4·OEt2 in acetic acid converts the aldehydes into their respective nitrile analogues which in situ undergo the Ritter reaction with diphenylmethanol or 1-adamantanol to afford the corresponding N-(diphenylmethyl)- or N-(1-adamantyl)amide derivatives in very good yields. The method does not require column chromatographic purification for isolation of the products. With its simple reaction procedure and easy product purification technique, this method outshines earlier conventional two-step methods.
Hazarika, Nabajyoti,Baishya, Gakul,Phukan, Prodeep
p. 2851 - 2859
(2015/09/15)

Comprehensive Study of the Organic-Solvent-Free CDI-Mediated Acylation of Various Nucleophiles by Mechanochemistry
Acylation reactions are ubiquitous in the synthesis of natural products and biologically active compounds. Unfortunately, these reactions often require the use of large quantities of volatile and/or toxic solvents, either for the reaction, purification or isolation of the products. Herein we describe and discuss the possibility of completely eliminating the use of organic solvents for the synthesis, purification and isolation of products resulting from the acylation of amines and other nucleophiles. Thus, utilisation of N,N′-carbonyldiimidazole (CDI) allows efficient coupling between carboxylic acids and various nucleophiles under solvent-free mechanical agitation, and water-assisted grinding enables both the purification and isolation of pure products. Critical parameters such as the physical state and water solubility of the products, milling material, type of agitation (vibratory or planetary) as well as contamination from wear are analysed and discussed. In addition, original organic-solvent-free conditions are proposed to overcome the limitations of this approach. The calculations of various green metrics are included, highlighting the particularly low environmental impact of this strategy.
Mtro, Thomas-Xavier,Bonnamour, Julien,Reidon, Thomas,Duprez, Anthony,Sarpoulet, Jordi,Martinez, Jean,Lamaty, Frdric
supporting information
p. 12787 - 12796
(2015/09/01)

A facile access for the C-N bond formation by transition metal-free oxidative coupling of benzylic C-H bonds and amides
Using 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) as the oxidant, we communicate an efficient oxidative C-N coupling of benzylic C-H bonds with amides to afford a series of amination products in good yields. A wide range of functional groups as well as various sulfonamides and carboxamides are well tolerated. Moreover, this reaction involves both the challenging C-H functionalization and C-N bond formation.
Liu, Jie,Zhang, Heng,Yi, Hong,Liu, Chao,Lei, Aiwen
p. 1323 - 1328
(2015/08/11)

Fe2(SO4)3·xH2O on silica: An efficient and low-cost catalyst for the direct nucleophilic substitution of alcohols in solvent-free conditions
Fe2(SO4)3·xH2O on silica has been found to be a novel efficient catalyst for the direct nucleophilic substitution of alcohols in solvent-free conditions. In this reaction system, the alcohols can react with various nucleophilic reagents for the convenient construction of C-C bonds and C-N bonds with the benefits of high conversion, no requirement to use excessive amounts of the nucleophile, only a catalytic amount of iron catalyst required, solvent-free and benign reaction conditions, and the feasible reusability of the catalyst.
Li, Lingjun,Zhu, Anlian,Zhang, Yuqin,Fan, Xincui,Zhang, Guisheng
p. 4286 - 4291
(2014/01/17)

Microwave assisted, Ca(II)-catalyzed Ritter reaction for the green synthesis of amides
An efficient solvent-free synthesis of amides by Ca(II) catalyzed Ritter reaction has been reported under microwave irradiation. This green protocol tolerates the substrate diversity and delivers the high yielding amides with minimal loading of inexpensive and more abundant Ca(II) catalyst.
Yaragorla, Srinivasarao,Singh, Garima,Lal Saini, Pyare,Reddy, M. Kesava
p. 4657 - 4660
(2014/12/10)

Peroxidation of C-H bonds adjacent to an amide nitrogen atom under mild conditions
Under mild conditions, the oxidative functionalization of C-H bonds adjacent to an amide nitrogen atom was achieved. tert-Butylperoxyamido acetal was obtained in high yields and could be further converted into α-substituted amides by treatment with Grigna
Yu, Hui,Shen, Jie
supporting information
p. 3204 - 3207
(2014/07/08)

Ritter reactions between alcohols and acetonitrile mediated by the conducting polymer poly-(3,4-ethylenedioxy thiophene) (Pedot)
Herein, we report new reactivity of the conducting polymer, poly-(3,4-ethylenedioxy thiophene) (PEDOT), where PEDOT mediates a Ritter reaction between alcohols and acetonitrile. The yields were variable and in most cases competitive with results obtained using sulfuric acid. Attempts at a stoichiometric reaction between benzonitrile and diphenylmethanol are also reported herein. Finally, described here are preliminary mechanistic studies that suggest PEDOT is behaving as an alcohol-selective or specific Lewis acid. Taylor & Francis Group, LLC.
D-Angelo, John G.,Cody, Jeremy A.,Larrabee, Christian,Ostrander, Danica J.,Rugg, Kyle W.,Mamangun, Donna
p. 3224 - 3232
(2014/01/06)

A Lewis acid palladium(II)-catalyzed three-component synthesis of α-substituted amides
A Lewis acid palladium-catalyzed reaction of amides, aryl aldehydes, and arylboronic acids is described. This new method allows for a practical and general synthesis of α-substituted amides from simple, readily available building blocks.
Beisel, Tamara,Manolikakes, Georg
supporting information
p. 6046 - 6049
(2014/01/06)

Aluminum triflate as a powerful catalyst for direct amination of alcohols, including electron-withdrawing group-substituted benzhydrols
Direct aminations of allylic alcohols, benzylic alcohols, and benzhydrols with electron-withdrawing (F, Br, I, NO2, or CN) substituents were efficiently catalyzed by aluminum triflate [Al(OTf)3] to afford the corresponding biarylamines in high yield, and the dibromo-substituted product was further transformed into letrozole. Copyright
Ohshima, Takashi,Ipposhi, Junji,Nakahara, Yasuhito,Shibuya, Ryozo,Mashima, Kazushi
supporting information
p. 2447 - 2452
(2012/11/07)

Sulfonic acid-functionalized ionic liquids as metal-free, efficient and reusable catalysts for direct amination of alcohols
A series of sulfonic acid-functionalized (SO3H-functionalized) ionic liquids was synthesized and used as metal-free, highly selective and efficient catalysts for the direct amination of alcohols. Notably, the activities of the series of SO3H-functionalized ionic liquids were compared and a 92% isolated yield was obtained using 3-tetradecyl-1-(butyl-4- sulfonyl)imidazolium trifluoromethanesulfonate ([BsTdIM][OTf]) as the catalyst. Importantly, the catalytic system has wide substrate scope including benzylic, allyl, propargylic, aliphatic alcohols with sulfonamide, amide, carbamate, aromatic amine and N-heterocyclic compounds. Interestingly, the system was also suitable for a multi-gram scale direct amination of alcohols. Additionally, the reusable nature of [BsTdIM][OTf] makes this protocol more attractive and avoids the disposal and neutralization of acidic catalysts. Moreover, preliminary experiments indicated that this reaction should proceed via an SN1 pathway. Copyright
Han, Feng,Yang, Lei,Li, Zhen,Xia, Chungu
experimental part
p. 1052 - 1060
(2012/05/21)

Ritter reaction in subcritical water: An efficient and green method for amides synthesis
Ritter reaction was carried out efficiently in subcritical water with catalytic amount of trifluoromethanesulfonic acid. The amides were formed in good to excellent yields from secondary alcohols and tert-butanol with various nitriles.
Jiang, Shengqian,Wang, Zhouyu,Jiang, Zhenju,Li, Jianhui,Zhou, Shulin,Pu, Long
experimental part
p. 24 - 28
(2012/08/08)

Ritter reactions in flow
Flow me a Ritter: Ritter reactions are performed in a simple microreactor setup using tert-butylacetate as versatile carbocation source. The protocol avoids the handling of large amounts of hot concentrated sulfuric acid as low concentrations are optimal for rapid access tert-butyl- or diphenylmethyl- protected amides. Copyright
Audiger, Logan,Watts, Kevin,Elmore, Simon C.,Robinson, Richard I.,Wirth, Thomas
experimental part
p. 257 - 260
(2012/05/04)

DDQ-mediated direct oxidative coupling of amides with benzylic and allylic sp3 C-H bonds under metal-free conditions
A simple and efficient method for the direct oxidative coupling of amides with benzylic and allylic sp3 C-H bonds using DDQ as an oxidant is described. A range of amides including benzamide, benzyl carbamate, and substituted sulfonamides reacted efficiently with various benzylic and allylic substrates under metal free conditions to afford amidation products in good to excellent yields.
Ramesh,Ramulu,Mukkanti,Venkateswarlu
experimental part
p. 2904 - 2908
(2012/07/27)

Au(iii)-catalyzed intermolecular amidation of benzylic C-H bonds
Au(iii)-catalyzed intermolecular amidations of benzylic C-H bonds with sulfonamides and carboxamides are described. The protocol with the Au-bipy complex/N-bromosuccinimide system provides practical applications for synthesis of various amides via C-H activations. The reaction proceeds with high efficiency to give the corresponding amines, which are extremely useful synthetic intermediates.
Zhang, Yan,Feng, Bainian,Zhu, Chengjian
supporting information
p. 9137 - 9141,5
(2012/12/12)

Efficient dehydrative C-N bond formation using alcohols and amides in the presence of silica supported perchloric acid as a heterogeneous catalyst
Silica supported perchloric acid has been utilized as an efficient heterogeneous recyclable catalyst for N-alkylation of amides (sulfonamides and carboxamides) using alcohols (primary and secondary aliphatic as well as benzylic). The products are formed in high yields within 2-3 h.
Das, Biswanath,Reddy, Parigi Raghavendar,Sudhakar, Chithaluri,Lingaiah, Maram
experimental part
p. 3521 - 3522
(2011/06/27)

HClO4-SiO2 as an efficient and recyclable catalyst for the synthesis of amide derivatives
An efficient and clean procedure for amide alkylation is reported by direct condensation of equimolar amounts of benzylic and allylic alcohols with primary amides in the presence of silica perchloric acid (HClO4-SiO 2). The direct co
Song, Weibin,Ma, Lei,Hu, Lihong
experimental part
p. 3186 - 3196
(2011/09/20)

Direct nucleophilic substitution reaction of alcohols mediated by a zinc-based ionic liquid
A zinc-based ionic liquid ([CHCl][ZnCl2]2) was found to be an excellent reaction medium for the direct nucleophilic substitution reactions of alcohols. The high conversion, high selectivity, easy separation procedure, catalyst reusability and no necessity of excessive nucleophiles make the chemical process cleaner. This reaction was believed to work through the carbocation mechanism and the existence of carbocation was detected by UV-vis spectroscopy. It was suggested that the hydroxyl group on the choline cation was the major inducement for the formation of special microstructures which could provide adequate stability for the carbocation in the reaction systems and increase the reactivity and selectivity.
Zhu, Anlian,Li, Lingjun,Wang, Jianji,Zhuo, Kelei
experimental part
p. 1244 - 1250
(2011/06/26)

Solvent-free amination of secondary benzylic alcohols with N-nucleophiles catalyzed by FeCl3
A general, simple, and environmentally friendly method for the direct amination of secondary benzyl alcohols with amides or 4-nitroaniline is described. This method has been applied to a variety of substrates, and the reaction proceeded smoothly at room temperature under solvent-free conditions. CbzNH2 was proved to be very useful in the direct preparation of the benzylic amines from corresponding alcohols.
Yu, Jian-Jun,Wang, Li-Min,Guo, Feng-Lou,Liu, Jin-Qian,Liu, Ying,Jiao, Ning
experimental part
p. 1609 - 1616
(2011/06/23)

Organocatalytic synthesis of amides from nitriles via the Ritter reaction
A simple, inexpensive, environmentally friendly, and efficient route for the synthesis of a wide variety of amides in high yields via the Ritter reaction of alcohols with nitriles has been demonstrated. Pentafluorophenyl ammonium triflate (PFPAT) is used as an organocatalyst and is air-stable, cost-effective, easy to handle, and easily removed from the reaction mixtures.
Khaksar, Samad,Fattahi, Eskandar,Fattahi, Esmail
experimental part
p. 5943 - 5946
(2011/11/28)

Sulfated tungstate: An efficient catalyst for the Ritter reaction
The use of sulfated tungstate as an efficient and reusable catalyst for the preparation of amides from alcohols and nitriles via the Ritter reaction pathway is discussed. The reaction proceeds under solvent free conditions. The Royal Society of Chemistry.
Katkar, Kamlesh V.,Chaudhari, Pramod S.,Akamanchi, Krishnacharya G.
supporting information; experimental part
p. 835 - 838
(2011/05/15)

Synthesis and characterization of N-benzhydrylbenzamide
Interaction of CD40 ligand (CD40L) with CD40 receptor is one of the most immunologically important interactions that involve in the regulation of T cell dependent B cell proliferation, differentiation and antibody production. Therefore, interfering CD40L interaction with CD40 may have important therapeutic applications. Using the three dimensional structure of CD40-CD40L complex, a small CD40L mimetic molecule, N-benzhydrylbenzamide was designed using computational techniques. This N-benzhydrylbenzamide was synthesized using Gabriel synthesis and Scotten-Baumann benzoylation reactions and characterized by FTIR and NMR spectroscopy. The FTIR spectrum of N-benzhydrylbenzamide shows the presence of various functional groups such as amide, aromatic groups and stretching vibrations for benzene derivatives. In addition, the 1H NMR spectrum of N-benzhydrylbenzamide confirmed the presence of amide and phenyl group hydrogens whereas the 13C NMR spectrum shows the presence of aromatic carbons and carbonyl group carbon. As the N-benzhydrylbenzamide structurally mimics CD40L, it can be considered as a candidate molecule for the further development of novel immunotherapeutic agent.
Vani, Vemula,Muthukumaran, Sivanandham
p. 2165 - 2168
(2012/03/10)

Cobalt-catalyzed benzylic C-H amination via dehydrogenative-coupling reaction
An efficient direct benzylic C-H amination via dehydrogenative-coupling by using an inexpensive catalyst/oxidant (CoBr2/tBuOO tBu) system is described. Various unmodified amides including primary or secondary sulfonamides, carboxamides, and carbamates preformed well with benzylic hydrocarbons with moderate to good yields.
Ye, Yang-Hong,Zhang, Ji,Wang, Gao,Chen, Shan-Yong,Yu, Xiao-Qi
supporting information; experimental part
p. 4649 - 4654
(2011/06/27)