- An unprecedented cobalt-catalyzed selective aroylation of primary amines with aroyl peroxides
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A novel and facile cobalt-catalyzed selective aroylation of primary amines with aroyl peroxides was developed for the synthesis of aryl amides. It was unprecedented that C[sbnd]N bond formation product was selectively generated without the common N[sbnd]O bond formation product. Aroyl peroxides act as the sole aroylation reagent without additional base or oxidant. The reactions proceeded under mild conditions and showed broad substrates scope with a series of primary amines and aroyl peroxides.
- Li, Dong,Li, Jiale,Li, Juanjuan,Yuan, Songdong,Zhang, Qian
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- Graphene oxide: A convenient metal-free carbocatalyst for facilitating amidation of esters with amines
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Herein, we report a graphene oxide (GO) catalyzed condensation of non-activated esters and amines, that can enable diverse amides to be synthesized from abundant ethyl esters forming only volatile alcohol as a by-product. GO accelerates ester to amide conversion in the absence of any additives, unlike other catalysts. A wide range of ester and amine substrates are screened to yield the respective amides in good to excellent yields. The improved catalytic activity can be ascribed to the oxygenated functionalities present on the graphene oxide surface which forms H-bonding with the reactants accelerating the reaction. Improved yields and a wide range of functional group tolerance are some of the important features of the developed protocol.
- Patel, Khushbu P.,Gayakwad, Eknath M.,Shankarling, Ganapati S.
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p. 2661 - 2668
(2020/02/20)
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- Graphene Oxide: A Metal-Free Carbocatalyst for the Synthesis of Diverse Amides under Solvent-Free Conditions
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An environmentally friendly, inexpensive, carbocatalyst, graphene oxide (GO) promoted efficient, metal-free transamidation of various carboxamides with aliphatic, cyclic, and aromatic amines is demonstrated. The protocol is equally applicable to phthalimide, urea, and thioamide determining its adaptability. The oxygenated functionalities such as carbonyl (?C=O), epoxy (?O?), carboxyl (?COOH) and hydroxyl (?OH), present on graphene oxide surface impart acidic properties to the catalyst. The graphene oxide being heterogeneous in nature, work efficiently under solvent-free reaction conditions providing desired products in good to excellent yields. The one-pot synthesis of 2,3-Dihydro-5H-benzo[b]-1,4-thiazepin-4-one moiety by GO catalyzed Aza Michael addition followed by intramolecular transamidation is also described. A plausible reaction mechanistic pathway involving H-bonding is discussed. The graphene oxide can be recycled and reused up to five cycles without much loss in catalytic activity. (Figure presented.).
- Patel, Khushbu P.,Gayakwad, Eknath M.,Patil, Vilas V.,Shankarling, Ganapati S.
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supporting information
p. 2107 - 2116
(2019/03/26)
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- Iridium-Catalyzed Benzylamine C-H Alkenylation Enabled by Pentafluorobenzoyl as the Directing Group
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The first iridium-catalyzed oxidative alkeynylation of benzylamines with acrylates enabled by a new directing group pentafluorobenzoyl has been developed. The reaction proceeded efficiently in the presence of silver acetate as oxidant and chlorobenzene as
- Yang, Xiao,Sun, Rui,Zhang, Chunchun,Zheng, Xueli,Yuan, Maolin,Fu, Haiyan,Li, Ruixiang,Chen, Hua
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supporting information
p. 1002 - 1006
(2019/02/19)
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- Highly Efficient Copper-Catalyzed Amidation of Benzylic Hydrocarbons Under Neutral Conditions
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A ligand free method has been developed for the amidation of benzylic hydrocarbons. A range of benzylic amides has been prepared with the use of dicumyl peroxide and a copper catalyst in good to excellent yields.
- Howard, Eva-Louise,Guzzardi, Norman,Tsanova, Viliyana G.,Stika, Angeliki,Patel, Bhaven
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supporting information
p. 794 - 797
(2018/02/21)
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- Copper nanoparticles on charcoal: An effective nanocatalyst for the synthesis of enol carbamates and amides via an oxidative coupling route
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The catalytic activity of copper nanoparticles on charcoal (Cu/C) was investigated as an environmentally friendly heterogeneous catalyst for the synthesis of enol carbamates and amides via the oxidative coupling of N,N-dialkyl formamides with 1,3-dicarbonyl compounds and aromatic aldehydes with amine hydrochloride salts, respectively. Various enol carbamates and amides were synthesized in moderate to good yields using this method. Moreover, the catalyst could be recovered and subsequently reused in further reactions.
- Saberi, Dariush,Mansoori, Sakineh,Ghaderi, Esmali,Niknam, Khodabakhsh
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supporting information
p. 95 - 99
(2015/12/23)
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- Tert -Butyl Peroxybenzoate Mediated Selective and Mild N-Benzoylation of Ammonia/Amines under Catalyst- and Solvent-Free Conditions
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A new protocol for the synthesis of amides from tert-butyl peroxybenzoate (TBPB) and ammonia/amines has been developed under catalyst- and solvent-free conditions. The ammonia, primary and secondary amines reacted smoothly with TBPB to furnish the corresponding primary, secondary, and tertiary amides in excellent yields. TBPB proved to be an efficient and highly chemoselective benzoylating reagent for aliphatic amines in the presence of aromatic amines/hydroxyl groups.
- Yadav, Dilip Kumar T.,Bhanage, Bhalchandra M.
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supporting information
p. 1862 - 1866
(2015/08/06)
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- C-N Coupling of Amides with Alcohols Catalyzed by N-Heterocyclic Carbene-Phosphine Iridium Complexes
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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.
- Kerdphon, Sutthichat,Quan, Xu,Parihar, Vijay Singh,Andersson, Pher G.
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p. 11529 - 11537
(2015/12/04)
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- A One-Pot, fast, and efficient amidation of carboxylic acids, α-amino acids and sulfonic acids using pph3/n-chlorobenzotriazole system
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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
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p. 1703 - 1714
(2015/09/15)
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- Bi(OTf)3-Catalyzed Multicomponent α-Amidoalkylation Reactions
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A bismuth(III) triflate catalyzed three-component synthesis of α-substituted amides starting from amides, aldehydes, and (hetero)arenes is reported. The reaction has a broad substrate scope, encompassing formaldehyde as well as aryl and alkyl aldehydes. Low catalyst loadings are required, and water is formed as the only side product. The scope and limitation of this method will be discussed.
- Schneider, Angelika E.,Manolikakes, Georg
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p. 6193 - 6212
(2015/06/30)
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- Bi(OTf)3-catalyzed three-component synthesis of amidomethylarenes and -heteroarenes
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A highly efficient Bi(OTf)3-catalyzed multicomponent synthesis of amidomethylated arenes and heteroarenes from readily available starting materials has been developed. This reaction proceeds under mild conditions, has a broad substrate scope, and in addition water is generated as only side product. Georg Thieme Verlag Stuttgart, New York.
- Schneider, Angelika E.,Manolikakes, Georg
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supporting information
p. 2057 - 2060
(2013/10/21)
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- PROCESS FOR PRODUCTION OF BIPHENYL DERIVATIVE
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The invention provides a production method of a biaryltetrazole derivative useful as an intermediate for an angiotensin II receptor antagonist. The method comprises reacting an aryltetrazole derivative with a benzene derivative, deprotecting or reducing the resulting compound, and halogenating the deprotected or reduced compound
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Page/Page column 18
(2012/09/22)
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- A fluorous Mukaiyama coupling reagent for a concise condensation reaction: Utility of medium-fluorous strategy
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The entire study of condensation reactions using various fluorous Mukaiyama reagents, including a novel medium-fluorous strategy, is described. A Mukaiyama reagent bearing a medium-fluorous content tag, between 40 and 60% fluorine by weight, was prepared and examined in ester and amide-forming condensation reactions. At the end of the reactions, the fluorous pyridone by-product was effectively separated from non-fluorous components by increasing the water content of the crude reaction mixture and subsequent filtration of the precipitate. It is also shown that Mukaiyama reagents bearing a fluorous tag increase the reaction rate considerably when compared to their non-fluorous tagged counterpart. Interestingly, it was observed that the longer the fluorous chain, the higher the activity of the Mukaiyama reagent.
- Sugiyama, Yuya,Kurata, Yuki,Kunda, Yoko,Miyazaki, Atsushi,Matsui, Junko,Nakamura, Shuichi,Hamamoto, Hiromi,Shioiri, Takayuki,Matsugi, Masato
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experimental part
p. 3885 - 3892
(2012/07/02)
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- Synthesis of angiotensin II receptor blockers by means of a catalytic system for C-H Activation
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A highly efficient catalytic system for C-H activation has been worked out that involves inexpensive RuCl3·xH2O and a specific amount of PPh3. This procedure has been successfully applied to a practical synthesis of angiotensin II receptor blockers (ARBs). The residual ruthenium that existed in the reaction mixture was thoroughly removed by treatment with properly selected metal scavengers. The new process permits ready access to the important class of drugs in a highly atom-economical and sustainable manner (Figure presented).
- Seki, Masahiko,Nagahama, Masaki
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experimental part
p. 10198 - 10206
(2012/02/03)
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- Preparation and condensation reactions of a new light-fluorous Mukaiyama reagent: reliable purification with fluorous solid phase extraction for esters and amides
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A modified light-fluorous Mukaiyama reagent bearing a C8F17 tag was prepared and examined in ester and amide forming condensation reactions. Following the reactions, the desired product was effectively separated from the fluorous pyridone by-product using a simple fluorous solid phase extraction.
- Matsugi, Masato,Hasegawa, Masakazu,Sadachika, Daisuke,Okamoto, Sachina,Tomioka, Mami,Ikeya, Yoshimi,Masuyama, Araki,Mori, Yuji
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p. 4147 - 4150
(2008/02/03)
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- Synthesis and biological evaluation of ebselen and its acyclic derivatives
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Five ebselen and three acyclic ebselen derivatives were synthesized. These compounds were screened for their glutathione peroxidase (GSH Px)-like activity and scavenging activity against 1,1-diphenyl-2-pycryl-hydrazyl (DPPH) and peroxynitrite radical. All tested compounds displayed similar significant GSH Px-like activity, which are slightly higher than that of ebselen. The peroxynitrite scavenging activity showed that the acyclic allylseleno 4c was five times more potent than ebselen.
- Chang, Tsu-Chung,Huang, Mei-Lan,Hsu, Wen-Lin,Hwang, Jing-Min,Hsu, Ling-Yih
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p. 1413 - 1416
(2007/10/03)
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