143572-98-9Relevant academic research and scientific papers
An unprecedented cobalt-catalyzed selective aroylation of primary amines with aroyl peroxides
Li, Dong,Li, Jiale,Li, Juanjuan,Yuan, Songdong,Zhang, Qian
, (2020/09/16)
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.
Graphene oxide: A convenient metal-free carbocatalyst for facilitating amidation of esters with amines
Patel, Khushbu P.,Gayakwad, Eknath M.,Shankarling, Ganapati S.
, p. 2661 - 2668 (2020/02/20)
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.
Graphene Oxide: A Metal-Free Carbocatalyst for the Synthesis of Diverse Amides under Solvent-Free Conditions
Patel, Khushbu P.,Gayakwad, Eknath M.,Patil, Vilas V.,Shankarling, Ganapati S.
supporting information, p. 2107 - 2116 (2019/03/26)
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.).
Iridium-Catalyzed Benzylamine C-H Alkenylation Enabled by Pentafluorobenzoyl as the Directing Group
Yang, Xiao,Sun, Rui,Zhang, Chunchun,Zheng, Xueli,Yuan, Maolin,Fu, Haiyan,Li, Ruixiang,Chen, Hua
supporting information, p. 1002 - 1006 (2019/02/19)
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
Highly Efficient Copper-Catalyzed Amidation of Benzylic Hydrocarbons Under Neutral Conditions
Howard, Eva-Louise,Guzzardi, Norman,Tsanova, Viliyana G.,Stika, Angeliki,Patel, Bhaven
supporting information, p. 794 - 797 (2018/02/21)
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.
Copper nanoparticles on charcoal: An effective nanocatalyst for the synthesis of enol carbamates and amides via an oxidative coupling route
Saberi, Dariush,Mansoori, Sakineh,Ghaderi, Esmali,Niknam, Khodabakhsh
supporting information, p. 95 - 99 (2015/12/23)
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.
Tert -Butyl Peroxybenzoate Mediated Selective and Mild N-Benzoylation of Ammonia/Amines under Catalyst- and Solvent-Free Conditions
Yadav, Dilip Kumar T.,Bhanage, Bhalchandra M.
supporting information, p. 1862 - 1866 (2015/08/06)
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.
Bi(OTf)3-Catalyzed Multicomponent α-Amidoalkylation Reactions
Schneider, Angelika E.,Manolikakes, Georg
, p. 6193 - 6212 (2015/06/30)
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.
A One-Pot, fast, and efficient amidation of carboxylic acids, α-amino acids and sulfonic acids using pph3/n-chlorobenzotriazole system
Rouhi-Saadabad, Hamed,Akhlaghinia, Batool
, p. 1703 - 1714 (2015/09/15)
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.
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.
