183198-63-2Relevant academic research and scientific papers
Efficient cleavage of tertiary amide bonds: Via radical-polar crossover using a copper(ii) bromide/Selectfluor hybrid system
Maruoka, Keiji,Matsumoto, Akira,Wang, Zhe
, p. 12323 - 12328 (2020/12/08)
A novel approach for the efficient cleavage of the amide bonds in tertiary amides is reported. Based on the selective radical abstraction of a benzylic hydrogen atom by a CuBr2/Selectfluor hybrid system followed by a selective cleavage of an N-C bond, an acyl fluoride intermediate is formed. This intermediate may then be derivatized in a one-pot fashion. The reaction proceeds under mild conditions and exhibits a broad substrate scope with respect to the tertiary amide moiety as well as to nitrogen, oxygen, and carbon nucleophiles for the subsequent derivatization. Mechanistic studies suggest that the present reaction proceeds via a radical-polar crossover process that involves benzylic carbon radicals generated by the selective radical abstraction of a benzylic hydrogen atom by the CuBr2/Selectfluor hybrid system. Furthermore, a synthetic application of this method for the selective cleavage of peptides is described. This journal is
Base-promoted amide synthesis from aliphatic amines and ynones as acylation agents through C-C bond cleavage
Cheng, Guolin,Lv, Weiwei,Kuai, Changsheng,Wen, Si,Xiao, Shangyun
supporting information, p. 1726 - 1729 (2018/02/21)
A new protocol for the synthesis of amides via base-promoted cleavage of the C(sp)-C(CO) bond of ynones with aliphatic primary and secondary amines under transition-metal-, ligand-, and oxidant-free conditions has been developed. This method exhibits a wide substrate scope, high functional group tolerance and exclusive chemoselectivity, as well as mild reaction conditions.
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.
Diboron-Catalyzed Dehydrative Amidation of Aromatic Carboxylic Acids with Amines
Sawant, Dinesh N.,Bagal, Dattatraya B.,Ogawa, Saeko,Selvam, Kaliyamoorthy,Saito, Susumu
supporting information, p. 4397 - 4400 (2018/08/09)
Tetrakis(dimethylamido)diboron and tetrahydroxydiboron are herein reported as new catalysts for the synthesis of aryl amides by catalytic condensation of aromatic carboxylic acids with amines. The developed protocol is both simple and highly efficient over a broad range of substrates. This method thus represents an attractive approach for the use of diboron catalysts in the synthesis of amides without having to resort to stoichiometric or additional dehydrating agents.
Repurposing n-butyl stannoic acid as highly efficient catalyst for direct amidation of carboxylic acids with amines
Potadar, Santoshkumar M.,Mali, Anil S.,Waghmode, Krishnakant T.,Chaturbhuj, Ganesh U.
supporting information, p. 4582 - 4586 (2018/11/27)
This is the first-time report on the repurposing n-butyl stannoic acid as a catalyst for direct amidation of carboxylic acids with amines. Notably, efficient amidation observed in comparison with all other catalytic methods reported up until now. The protocol has successfully applied to the synthesis of a variety of amides. Moderate reaction parameters, clean amidation with excellent yields of desired amides, ability to tolerate a variety of functional groups, easy product isolation; commercial availability and recyclability of the catalyst are key advantages of the current protocol.
AMIDATION METHOD AND ESTERIFICATION METHOD USING SULFONIC ACID HALIDE
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Paragraph 0038, (2017/01/17)
PROBLEM TO BE SOLVED: To provide a safe and economical method for rapidly synthesizing amides and esters in high yield. SOLUTION: There is provided a method for amidating an amine or a derivative thereof using a sulfonic acid halide, where a sulfonic acid halide is allowed to act as an activator on a carboxylic acid or a derivative thereof to synthesize an active ester, and the active ester is reacted with an amine or a derivative thereof as a nucleophile to amidate the amine or the derivative thereof to obtain a corresponding amide or a derivative thereof. In a similar manner, a sulfonic acid halide is allowed to act as an activator on a carboxylic acid or a derivative thereof to synthesize an active ester, and the active ester is reacted with an alcohol or a derivative thereof as a nucleophile to esterify the alcohol or the derivative thereof to obtain a corresponding ester or a derivative thereof. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2016,JPO&INPIT
Easy, Green and Safe Carbonylation Reactions through Zeolite-Catalyzed Carbon Monoxide Production from Formic Acid
Losch, Pit,Felten, Anne-Sophie,Pale, Patrick
supporting information, p. 2931 - 2938 (2015/09/28)
Zeolites with the right shape and acid site density and strength, such as certain ZSM-5 forms, were able to cleanly decompose formic acid to carbon monoxide (CO), and the latter could be directly used in palladium-catalyzed carbonylation reactions. A simple two-reactor system was designed to produce CO conveniently and then further react this gas in a safe way. The two-reactor system is particularly cheap, easy to set up and use. In addition, the carbonylation conditions without pressure allowed for very efficient CO incorporation, with only 1% of palladium(II) chloride (PdCl2) and Xantphos.
Palladium-catalyzed fluorocarbonylation using N-formylsaccharin as CO source: General access to carboxylic acid derivatives
Ueda, Tsuyoshi,Konishi, Hideyuki,Manabe, Kei
supporting information, p. 5370 - 5373 (2013/11/06)
N-Formylsaccharin, an easily accessible crystalline compound, has been employed as an efficient CO source in Pd-catalyzed fluorocarbonylation of aryl halides to afford the corresponding acyl fluorides in high yields. The reactions use a near-stoichiometric amount of the CO source (1.2 equiv) and tolerate diverse functional groups. The acyl fluorides obtained could be readily transformed into various carboxylic acid derivatives such as carboxylic acid, esters, thioesters, and amides in a one-pot procedure.
A simple base-mediated amidation of aldehydes with azides
Kulkarni, Sameer S.,Hu, Xiangdong,Manetsch, Roman
supporting information, p. 1193 - 1195 (2013/03/13)
A practical and efficient amidation reaction involving aromatic aldehydes and various azides under mild conditions is described. A broad spectrum of functional groups was tolerated, and the amides were synthesized in moderate to excellent yields, presenting an attractive alternative to the currently available synthetic methods.
Photochemically induced synthesis of the topoisomerase i inhibitors indeno [1,2-c]isoquinoline-5,11-diones
Dubois, Mélanie,Deniau, Eric,Couture, Axel,Grandclaudon, Pierre
scheme or table, p. 1047 - 1051 (2012/06/17)
A convenient synthesis of indeno[1,2-c]isoquinoline-5,11-diones has been achieved using combinational photochemical and carbocationic cyclization tactics. The synthetic route involved first the construction of adequately functionalized N-styryl benzamides via Suzuki-Miyaura cross-coupling reaction with enol phosphate combined with a six - electron photocyclization process. The assembling of the title compounds was readily ensured through sequential carbocationic annulation reaction and ultimate oxidation of a latent hydroxy functionality. Georg Thieme Verlag Stuttgart · New York.
