41882-53-5Relevant 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.
Nickel-catalyzed reductive amidation of aryl-triazine ethers
Heravi, Majid M.,Panahi, Farhad,Iranpoor, Nasser
supporting information, p. 1992 - 1995 (2020/02/22)
The reaction of activated phenolic compounds, 2,4,6-triaryloxy-1,3,5-triazine (aryl-triazine ethers), with various isocyanates or carbodiimides in the presence of a nickel pre-catalyst resulted in the synthesis of aryl amides in good to excellent yields.
Base-Promoted Amidation and Esterification of Imidazolium Salts via Acyl C-C bond Cleavage: Access to Aromatic Amides and Esters
Karthik, Shanmugam,Muthuvel, Karthick,Gandhi, Thirumanavelan
, p. 738 - 751 (2019/01/24)
Imidazolium salts have been effectively employed as suitable acyl transfer agents in amidation and esterification in organic synthesis. The weak acyl C(O)-C imidazolium bond was exploited to generate acyl electrophiles, which further react with amines and alcohols to afford amides and esters. The broad substrate scope of anilines and benzylic amines and base-promoted conditions are the benefits of this route. Interestingly, phenol, benzylic alcohols, and a biologically active alcohol can also be subjected to esterification under the optimized conditions.
Hydrogen Bond Directed ortho-Selective C?H Borylation of Secondary Aromatic Amides
Bai, Shao-Tao,Bheeter, Charles B.,Reek, Joost N. H.
supporting information, p. 13039 - 13043 (2019/07/31)
Reported is an iridium catalyst for ortho-selective C?H borylation of challenging secondary aromatic amide substrates, and the regioselectivity is controlled by hydrogen-bond interactions. The BAIPy-Ir catalyst forms three hydrogen bonds with the substrate during the crucial activation step, and allows ortho-C?H borylation with high selectivity. The catalyst displays unprecedented ortho selectivities for a wide variety of substrates that differ in electronic and steric properties, and the catalyst tolerates various functional groups. The regioselective C?H borylation catalyst is readily accessible and converts substrates on gram scale with high selectivity and conversion.
A solid-supported arylboronic acid catalyst for direct amidation
Du, Yihao,Barber, Thomas,Lim, Sol Ee,Rzepa, Henry S.,Baxendale, Ian R.,Whiting, Andrew
supporting information, p. 2916 - 2919 (2019/03/27)
An efficient heterogeneous amidation catalyst has been prepared by co-polymerisation of styrene, DVB with 4-styreneboronic acid, which shows wide substrate applicability and higher reactivity than the equivalent homogeneous phenylboronic acid, suggesting potential cooperative catalytic effects. The catalyst can be easily recovered and reused; suitable for use in packed bed flow reactors.
An efficient transformation of methyl ethers and nitriles to amides catalyzed by Iron(III) perchlorate hydrate
Yin, Guibo,Yan, Bin,Chen, Junqing,Ji, Min
, p. 1355 - 1363 (2019/04/30)
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.
An efficient, one-pot transamidation of 8-aminoquinoline amides activated by tertiary-butyloxycarbonyl
Wu, Wengang,Yi, Jun,Xu, Huipeng,Li, Shuangjun,Yuan, Rongxin
, (2019/04/05)
The efficient, one-pot access to the transamidation of 8-aminoquinoline (8-AQ), notorious for its harsh removal conditions, has been widely employed as an auxiliary in C–H functionalization reactions due to its strong directing ability. In this study, the facile and mild Boc protection of the corresponding 8-AQ amide was critical to activate the amide C(acyl)–N bond by twisting its geometry to lower the amidic resonance energy. Both aryl and alkyl amines proceeded transamidation in one-pot, user-friendly conditions with excellent yields.
FeCl2·4H2O catalyzed ritter reaction with nitriles and halohydrocarbons
Feng, Cheng-Liang,Yin, Gui-Bo,Yan, Bin,Chen, Jun-Qing,Ji, Min
, p. 345 - 353 (2019/02/12)
An efficient and inexpensive synthesis of N-substituted amides from the Ritter reaction of nitriles with various halohydrocarbons catalyzed by FeCl2·4H2O is described. FeCl2·4H2O economically efficiently catalyzed the Ritter reaction under solvent-free conditions. A range of halohydrocarbons (benzyl, tert-butyl and sec-alkyl halohydrocarbons) were coupled with nitriles to provide the corresponding amides in high to excellent yields.
Fe(ClO 4) 3 ·h 2 O-Catalyzed Ritter Reaction: A Convenient Synthesis of Amides from Esters and Nitriles
Feng, Chengliang,Yan, Bin,Yin, Guibo,Chen, Junqing,Ji, Min
, p. 2257 - 2264 (2018/10/20)
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.
Functional Group Transposition: A Palladium-Catalyzed Metathesis of Ar-X σ-Bonds and Acid Chloride Synthesis
De La Higuera Macias, Maximiliano,Arndtsen, Bruce A.
supporting information, p. 10140 - 10144 (2018/08/23)
We describe the development of a new method to use palladium catalysis to form functionalized aromatics: via the metathesis of covalent σ-bonds between Ar-X fragments. This transformation demonstrates the dynamic nature of palladium-based oxidative addition/reductive elimination and offers a straightforward approach to incorporate reactive functional groups into aryl halides through exchange reactions. The reaction has been exploited to assemble acid chlorides without the use of high energy halogenating or toxic reagents and, instead, via the metathesis of aryl iodides with other acid chlorides.
