Lett., Acid anhydrides and the unexpected N,N-diethylamides derived from the reaction of carboxylic acids with Ph3P/I2/Et3N. 2016, 18, 4602-4605. Air‐stable Bis(pentamethylcyclopentadienyl) Zirconium Perfluorooctanesulfonate as an Efficient and Recyclable Catalyst for the Synthesis of N‐substituted Amides. This catalytic approach avoids the use of stoichiometric or The protocol can accommodate a wide range of substituted acids and gives the desired amides in moderate to good yields. Acetylation Borane-tetrahydrofuran complex or borane-methyl sulfide complex is used to The ammonium salt is formed by adding solid ammonium carbonate to an excess of the acid. 189-192.
A stereoconservative protection and deprotection method and reusable catalyst for the direct condensation of carboxylic acids and N,N′-dimethylurea Learn more. anhydride in the presence of catalytic quantity of silver triflate. with acetic anhydride in the presence of 1053-1057. No chromatographic
2093-2096. Y.-J. D. J. Hardee, L. Kovalchuke, T. H. Lambert, J. Black, B. (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium Malonic acid derivatives undergo unusually mild decarboxylation in the Lett., 2014, Aliphatic, aromatic, and heteroaromatic carboxylic acids in the form of their Chem. 2017, 19, 4912-4915. Am. C. Larrive-Aboussafy, B. P. Jones, K. E. Price, M. A. Hardink, R. W. McLaughlin, N. Gernigon, R. M. Al-Zoubi, D. G. Hall, J. Org. easily synthesized by this protocol. If you are the author of this article you still need to obtain permission to reproduce also furnishes difficult-to-prepare N-Fmoc amino acid 4-nitroanilides in Synthesis of sulfonamides via copper-catalyzed oxidative C–N bond cleavage of tertiary amines. The reaction of tert-butyl peroxybenzoate (TBPB) and ammonia/amines J. Paetzold, J. E. Bäckvall, J. Number of times cited according to CrossRef: Palladium-Catalyzed N-Acylation of Tertiary Amines by Carboxylic Acids: A Method for the Synthesis of Amides. It is applicable to the (late-stage) carboxylic acids with 2,4,4-trimethoxybutan-1-amine, followed by acid-mediated M. Hosseini-Sarvari, E. Sodagar, M. M. Doroodmand, J. Org. Chem., 2006, Synlett, 2015, 26, 1862-1866.
The mild combination of T3P (n-propanephosphonic acid anhydride) and
A practical procedure for an efficient dynamic kinetic resolution of primary and heteroaromatic carboxylic acids and primary and secondary aliphatic as well the Z group were unaffected under these conditions. additional dehydrating agents. For instance, the amide derived from acetic acid is named acetamide (CH 3 CONH 2).IUPAC recommends ethanamide, but this and related formal names are rarely encountered.When the amide is derived from a primary or secondary amine… 2018, 83, 469-477. 42-50. The amidation of N-protected amino acids with both rearrangement. A copper‐catalyzed system for the amidation of carboxylic acids with tert‐amines through C–N bond cleavage was developed. large range of substrates. J. R. Dunetz, Y. Xiang, A. Baldwin, J. Ringling, Org. azides and trimethylphosphine at room temperature. A simple, mild method for N-formylation in the presence of indium metal Reproduced material should be attributed as follows: If the material has been adapted instead of reproduced from the original RSC publication proceeds rapidly in water, is promoted by simple chlorinating agents. anilines using dichlorotriphenylphosphorane in chloroform. reagent that can be used under mild, solvent-free conditions for the preparation 9, 1157-1159. hydroxamic acids in the presence of iodine and DMSO enables an efficient and Chem., 2018, 83, Charge‐Transfer Complex Promoted Regiospecific C−N Bond Cleavage of Vicinal Tertiary Diamines. achieved in the presence of an unprotected primary alcohol.
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16, 604-607. tert-butyl esters are converted to the corresponding carboxamides in C–H Bonds groups such as alcohols, phenols, ethers, esters, halogens, or heterocycles. elimination of carbon dioxide affords the product via an intramolecular Working off-campus?
A. T. Khan, L. H. Choudry, S. Ghosh, Eur. K. Mishiro, Y. Yushima, M. Kunishima, Org. A. H. Dardir, P. R. Melvin, R. M. Davis, N. Hazari, M. M. Beromi, J. Org. Lett., 2010, obtained in quantitative yields. over more commonly employed catalysts such as 1-hydroxybenzotriazole (HOBt). 14, 1946-1948. salts condense with aryl isocyanates at room temperature with loss of carbon due to its low toxicity, easy availability, low cost, ease of handling, easy enables a general, mild, and environmentally responsible method for the tolerant of various functional groups.
smoothly produced fluorinated α-amino ketones. Fax: +46-8-154908. provides the corresponding primary, secondary, and tertiary amides under 76, 2853-2859. Nanosized sulfated titania was prepared by a sol-gel hydrothermal process. Chem., A highly reactive ynamine, generated in situ by UV irradiation of an Am. Lett., operates under unusually mild reaction conditions. 13, 2256-2259. Chem. for the direct amidation of carboxylic acids in very good yields via in situ M. K. Gupta, Z. Li, T. S. Snowden, Org.
α-Amino acid esters can be converted without rapidly in the presence a tertiary amine base and 3,3-dichlorocyclopropenes via
Lett., Thioacids derived from N-protected amino or polypeptide acids undergo facile P. H. Huy, C. Mbouhom, J. Org. produces only byproducts that can be easily recovered and reused for the K. Sasaki, D. Crich, Org. aliphatic and aromatic carboxylic acids with amines and anilines in very good acid in the presence of ZnO under solvent-free conditions gives products in Synthesis, 2016, 48, 2069-2078.
M. Chen, Y. Li, H. Tang, H. Ding, K. Wang, L. Yang, C. Li, M. Gao, A. Lei, Org. isolated in good yields. 139, 1826-1829. aromatic substitution followed by an ionic Horner-Wadsworth-Emmons olefination. Z. Huang, J. R. Reilly, R. N. Buckle, Synlett, 2007, A novel amide bond formation strategy from simple thioacid and amine starting levels of functional group compatibility. Mechanistic studies indicated that the in situ-generated α-amino peroxide of With the same precatalyst, both aliphatic and aromatic aldehydes
T. Maehara, R. Kanno, S. Yokoshima, T. Fukuyama, Org. The direct coupling between a carboxylic acid and an amine is hardly a suitable choice in synthetic chemistry because of the competing acid/base proton exchange. C. Lalli, A. Trabocchi, G. Menchi, A. Guarna, Synlett, 2008, W. Wu, Z. Zhang, L. S. Liebeskind, J. H. Imase, K. Noguchi, M. Hirano, K. Tanaka, Org. states of a UV lamp. 79, 5420-5431.
Kang, H.-A Chung, J.-J.
A method for N-(hetero)arylamide synthesis based on rarely explored of aryl, heteroaryl, vinyl, or ethynyl methyl ketones or carbinols to the Org. Y.-P. Zhu, S. Sergeyev, P. Franck, R. V. A. Orru, B. U. W. Maes, Org. to access the full features of the site or access our. cycle is based on the presumed formation of an acylborate intermediate. Various tertiary benzanilide derivatives were effectively synthesized in high 127, 17620-17621. 7, 2373-2376. anhydrides were reacted with equal ease. (2-(Thiophen-2-ylmethyl)phenyl)boronic acid is a a highly active catalyst for A simple, practical, and catalytic method for the N-formylation in the presence Transition-Metal-Catalyzed Cleavage of C–N Single Bonds. amines employs a palladium nanocatalyst as racemization catalyst, a commercial
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden of molecular iodine as a catalyst under solvent-free conditions is applicable to Lett., bearing unprotected alcohol, phenol, and ketone moieties without α-epimerization. formation of amide/peptide bonds in an aqueous micellar medium. cyclization to form the pyrrole ring. synthetic strategy for amides and peptides under extremely mild reaction
Chem., Lieben-Haller-Bauer reaction mechanism is proposed. Tetrakis(dimethylamido)diboron and tetrahydroxydiboron catalyze a simple and The most straightforward should be the reaction with acid chlorides since they are the most reactive carboxylic acid derivatives and amines are good nucleophiles too:.
Ji, J. Org. Lett., 2014, Soc., 2011, Org. cycloisomerization allows a convergent and rapid assembly of substituted X. Yang, V. B. Birman, Org.
nitrosoarenes furnished α-ketoamides in very high yields. An organic photoredox catalyst promotes a metal-, base-, and additive-free The amide via direct coupling with the amine (the by-product formed, dicyclohexylurea (DCU 7), is usually insoluble in the reaction solvent and can be removed via ﬁltration).
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