27285-18-3Relevant academic research and scientific papers
Graphene oxide-catalyzed CSp3–H activation of methylarenes in aqueous medium: A unified metal-free access to amides and benzimidazoles
Dandia, Anshu,Mahawar, Dinesh Kumar,Sharma, Ruchi,Badgoti, Ranveer Singh,Rathore, Kuldeep S.,Parewa, Vijay
, (2019/09/12)
Graphene oxide (GO)-catalyzed selective synthesis of amides via CSp3–H activation of methylarenes and consequent C–N bond formation with anilines under aqueous medium has been described. Oxygen functionality allied with GO surface played a dual role both as acid catalyst and oxidizing agent to some extent. However, GO has a copious effect on the reaction, shown by a high TOF value with TBHP as co-oxidant. The decisive role of carboxylic acid functional groups on GO nanosheets in this metal-free strategy has been confirmed and was monitored by various analytic techniques viz. Fourier transform-infrared, UV–Vis, Raman and XPS. A plausible mechanism was proposed by control experiments and by the isolation of the intermediate. Over-oxidation of methylarenes was not detected, and high recyclability of the carbocatalyst with its heterogeneous behavior facilitated the isolation and purification of the desired products. We have further explored the utility of this process for the chemoselective synthesis of benzimidazoles.
Metal-Free Sustainable Synthesis of Amides via Oxidative Amidation Using Graphene Oxide as Carbocatalyst in Aqueous Medium
Dandia, Anshu,Parihar, Sonam,Saini, Pratibha,Rathore, Kuldeep S.,Parewa, Vijay
, p. 3169 - 3175 (2019/07/30)
Abstract: We describe an efficient, clean and metal-free procedure for the synthesis of amides via oxidative amidation of aldehydes with anilines using graphene oxide (GO) as a recyclable catalyst and KBrO3 as a mild oxidant in aqueous medium under microwave irradiation. GO nanosheets were prepared and characterized by XRD, TEM, SEM, and FT-IR, analyses. GO showed high compatibility with KBrO3 in water and offered high TOF value (1.30 × 10?3 mol?g?1 min?1). GO oxygen functionalities catalyze the oxidative amidation effectively in mild condition with high recyclability. A plausible mechanism was proposed by the isolating the intermediate. Graphic Abstract: [Figure not available: see fulltext. ]
The use of Cr (CO)6 as an alternative CO source in Pd-catalyzed C-N bond formation: Synthesis of benzamides
Mozaffari, Mozhdeh,Nowrouzi, Najmeh,Abbasi, Mohammad
, (2019/06/27)
An efficient strategy for the synthesis of benzamides from acetamides and aryl iodides using 1?mol% Pd (OAc)2 as catalyst and Cr (CO)6 as CO-precursor is described. This new synthetic methodology displays high functional group tolerance on both substrates and avoids the need for ligands, reducing agents, or other additives. The corresponding products were obtained in good to excellent yields at atmospheric pressure under mild reaction conditions.
Triflic anhydride mediated synthesis of 3,4-dihydroquinazolines: A three-component one-pot tandem procedure
Magyar, Christina L.,Wall, Tyler J.,Davies, Steven B.,Campbell, Molly V.,Barna, Haven A.,Smith, Sydney R.,Savich, Christopher J.,Mosey, R. Adam
supporting information, p. 7995 - 8000 (2019/09/06)
A one-pot three-component tandem reaction involving a key Pictet-Spengler-like annulation step has been developed, providing an efficient method for the synthesis of 3,4-dihydroquinazolines in moderate to good yields from amides, aldehydes, and amines. The multicomponent triflic anhydride mediated reaction tolerates the installation of numerous functional groups, affording extensive diversity about the heterocyclic scaffold.
Accelerated Discovery in Photocatalysis using a Mechanism-Based Screening Method
Hopkinson, Matthew N.,Gómez-Suárez, Adrián,Teders, Michael,Sahoo, Basudev,Glorius, Frank
supporting information, p. 4361 - 4366 (2016/04/05)
Herein, we report a conceptually novel mechanism-based screening approach to accelerate discovery in photocatalysis. In contrast to most screening methods, which consider reactions as discrete entities, this approach instead focuses on a single constituent mechanistic step of a catalytic reaction. Using luminescence spectroscopy to investigate the key quenching step in photocatalytic reactions, an initial screen of 100 compounds led to the discovery of two promising substrate classes. Moreover, a second, more focused screen provided mechanistic insights useful in developing proof-of-concept reactions. Overall, this fast and straightforward approach both facilitated the discovery and aided the development of new light-promoted reactions and suggests that mechanism-based screening strategies could become useful tools in the hunt for new reactivity. Enlightened! A mechanism-based screening approach can accelerate discovery in photocatalysis. It focuses on a single mechanistic step of a reaction class: the quenching step central to photocatalytic transformations. Luminescence spectroscopy was used to screen 100 compounds, identifying two promising substrate classes. A second, more-focused screen provided mechanistic insights for developing proof-of-concept reactions.
Para-Selective C-H Amidation of Simple Arenes with Nitriles
Xiang, Shi-Kai,Li, Jin-Mei,Huang, He,Feng, Chun,Ni, Hai-Liang,Chen, Xiao-Zhen,Wang, Bi-Qin,Zhao, Ke-Qing,Hu, Ping,Redshaw, Carl
, p. 3435 - 3440 (2016/01/25)
A para-selective C-H amidation of simple arenes with nitriles has been developed. By increasing the amount of arenes, a further meta-selective C-H arylation of the produced amides occurred. Both steric and electronic effects are utilized to control the selectivity, resulting in only para-selective amidation products. The readily available nitriles as amidation reagents instead of amides makes the synthesis of N-arylamides more accessible.
Ce(III) immobilised on aminated epichlorohydrin-activated agarose matrix - "green" and efficient catalyst for transamidation of carboxamides
Zarei, Zeinab,Akhlaghinia, Batool
, p. 1421 - 1437 (2015/09/15)
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.
Synthesis of amides through an oxidative amidation of tetrazoles with aldehydes under transition-metal-free conditions
Du, Juan,Luo, Kai,Zhang, Xiuli
, p. 54539 - 54546 (2015/01/09)
A simple, inexpensive and efficient one-pot synthesis of amides was achieved in good yields via the direct oxidative amidation of tetrazoles with aldehydes under transition-metal-free conditions.
Copper-catalyzed dehydrogenative cross-coupling reactions of N-para-tolylamides through successive C-H activation: Synthesis of 4H-3,1-benzoxazines
Xiong, Tao,Li, Yan,Bi, Xihe,Lv, Yunhe,Zhang, Qian
supporting information; experimental part, p. 7140 - 7143 (2011/09/12)
A novel annulation reaction of readily available tolylamides was catalyzed by Cu(OTf)2 in the presence of Selectfluor and water through successive intermolecular C-H activated dehydrogenative cross-coupling reactions of benzylic methyl C(sp3)-H and aromatic C(sp2)-H bonds, and subsequent intramolecular C-O bond formation (see scheme). Copyright
Palladium-catalyzed oxidative C-H bond acylation of acetanilides with benzylic alcohols
Yuan, Yu,Chen, Duanteng,Wang, Xiaowei
supporting information; experimental part, p. 3373 - 3379 (2012/02/03)
An efficient and clean method to construct C-C bonds has been developed via the acylation reaction of acetanilides with benzylic alcohols using tert-butyl hydroperoxide (TBHP) as oxidant catalyzed by palladium acetate in the presence of triflic acid (TfOH). The acylation reactions exhibit excellent reactivities, and up to 95% yield of the corresponding aryl ketone could be obtained under the optimal conditions. Copyright
