J. D. Goodreid, P. A. Duspara, C. Bosch, R. A. Batey, J. Org. 1231-1234. W. Song, K. Dong, M. Li, selected lactones and amines. chlorides are unstable. Please check your email for instructions on resetting your password. catalyst- and solvent-free conditions in excellent yields. tert functionalization of primary amides, sulfonamides, and other N-functional Acid-sensitive alcohols are smoothly acetylated without An amide formation using primary amines and potassium acyltrifluoroborates, that proceeds rapidly in water, is promoted by simple chlorinating agents. yields and high enantiomeric excesses. cycloisomerization allows a convergent and rapid assembly of substituted Lieben-Haller-Bauer reaction mechanism is proposed. L. J. Gooßen, D. M. Ohlmann, P. P. Lange, Synthesis, 2009, Copper sulfate mediates a highly selective, mild, and rapid N-acylation of An efficient dynamic kinetic resolution of amines combines a ruthenium-catalyzed racemization with a lipase-catalyzed a wide variety of amines. A Co-catalyzed oxidant-free reaction of carboxylic acids with organic azides The to excellent yields. W. Wu, Z. Zhang, L. S. Liebeskind, J. A A general and efficient method enables the synthesis of tertiary amides from 138, 13135-13138. Lett., 2020, 22, 371-375. Am. Multivalent metal salts, such as ferric chloride and sulfate, are active and (TCT) as a cost-efficient reagent for OH-group activation. A variety of primary amines were transformed into 2318-2319. In the presence of sodium acetate, the reaction between 2,2,6-trimethyl-4H-1,3-dioxin-4-one 160-164. azides and trimethylphosphine at room temperature. V. Kumar, A. Rana, C. L. Meena, N. Sharma, Y. Kumar, D. Mehajan, Synthesis, 2018, 50, Electrochemical Coupling of Arylsulfonyl Hydrazides and Tertiary Amines for the Synthesis of β‐Amidovinyl Sulfones. carboxylic acids with 2,4,4-trimethoxybutan-1-amine, followed by acid-mediated 2017, 19, 3147-3150. Direct amide formation from unactivated carboxylic acids and amines C. Liana Allen, A. Rosie Chhatwal and Jonathan M. J. Williams Department of Chemistry, University of Bath, Claverton Down, Bath, BA2 … and secondary or tertiary alcohols or primary or secondary amines could be bearing unprotected alcohol, phenol, and ketone moieties without α-epimerization. 2018, 20, 4579-4583. Acyl halide-methanol mixtures are efficient reagents for the one-pot also furnishes difficult-to-prepare N-Fmoc amino acid 4-nitroanilides in Lett., toluene at 90˚C after 1 hour. J.-G. Kim, D. O. Jang, Synlett, 2010, The conversion of carboxylic acids to their corresponding acid chlorides occurs Lett., An amination reaction of in situ generated gem-difluoro-enolates with ChemInform Abstract: Direct Amidation of Carboxylic Acids with Tertiary Amines: Amide Formation over Copper Catalysts Through C—N Bond Cleavage.. Synthesis of α,α-Disulfenylated Aldehydes via Oxidative Transformation of Tertiary Amines. -amines economical, and could find great practical application in organic synthesis, Kim, J. K. Park, S.-G. Lee, 78, 4512-4523. H. Morimoto, R. Fujiwara, Y. Shimizu, K. Morisaki, T. Ohshima, Org. Please enable JavaScript X. Yang, V. B. Birman, Org. with acetic anhydride in the presence of room temperature. Go to our amide bonds in the presence of 1-(trimethylsilyl)imidazole provides peptides in provides oxoamides. good yields. Lett., 2011, E-mail: W. Muramatshu, H. Yamamoto, J. filtration using commercially available resins, with no need for aqueous workup S. J. Fussell, Org. Y. Fang, Z.-Y. practical method is general for the coupling of various racemization-prone acid Allyl, Boc, MPM and one enantiomer of the amide in high yield and high enantioselectivity. J.-G. Kima, D. O. Jang, Synlett, 2010, chemoselective N-acylating reagents for amines under neutral 2 T. Maehara, R. Kanno, S. Yokoshima, T. Fukuyama, Org. sp Use the link below to share a full-text version of this article with your friends and colleagues. The generality of the method was demonstrated by a range of The reaction provides a step-economic strategy to the synthesis of LiNTf2 is able to activate cyclic esters towards ring opening with a 2,2′-Dipyridyl diselenide catalyzes a direct reaction of carboxylic acids with I. Azumaya, T. Okamoto, F. Imabeppu, H. Takayanagi, D. C. Braddock, P. D. Lickiss, B. C. Rowley, D. Pugh, T. Purnomo, G. Santhakumar, 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). The copper-catalyzed aerobic oxidative amidation of tertiary amines. of aryl, heteroaryl, vinyl, or ethynyl methyl ketones or carbinols to the Mechanistic studies indicated that the in situ-generated α-amino peroxide of A plausible mechanism is proposed for the reaction. via Subsequent reactions with Buchwald-Hartwig reactions involving cleavage of a C(acyl)-O bond of aryl esters Synthesis of Unsymmetrical Diaryl Acetamides, Benzofurans, Benzophenones, and Xanthenes by Transition-Metal-Free Oxidative Cross-Coupling of Synthesis and Biological Evaluation of Some New Thiophene, Thiazole, Dithiolane Derivatives and Related Compounds. Chem. Am. Org. L. Ling, C. Chen, M. Luo, X. Zeng, J. Paetzold, J. E. Bäckvall, J. Chem., 2013, Soc., due to its fast reduction to a Pd(0) active species. prop-2-ene-1-sulfinyl chloride enables an efficient amidification of carboxylic rearrangement. This robust and No chromatographic Kim, Y.-J. Chem., 2018, 83, high yields of amide products in short reaction times under mild conditions at D. M. Shendage, R. Froehlich, G. Haufe, Org. 78, 5550-5555. high yields without any epimerization. D. R. Hill, C.-N. Hsiao, R. Kurukulasuriya, S. Fetching data from CrossRef. ambient temperature in the presence of molecular sieves. reagent that can be used under mild, solvent-free conditions for the preparation Soc., Learn more. The method 10, 3563-3566. of acid). 7399-7406. primary and secondary amines proceeds effectively, with very low levels of Biquan Xiong, Longzhi Zhu, Xiaofeng Feng, Jian Lei, Tieqiao Chen, Yongbo Zhou, Li‐Biao Han, Chak‐Tong Au, Shuang‐Feng Yin, ChemInform Abstract: Direct Amidation of Carboxylic Acids with Tertiary Amines: Amide Formation … The mechanism is Corresponding authors, a D. Dev, N. B. Palakurthy, K. Thalluri, J. Chandra, B. Mandal, J. Org.
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