Inorganic Chemistry , 56 17 , Aponte, Jamie E. Elsila, Daniel P. Glavin, Stefanie N. Milam, Steven B. Charnley, and Jason P. Pathways to Meteoritic Glycine and Methylamine. Jeff Joseph A. Herron, and Travis J. ACS Catalysis , 7 2 , Chemical Reviews , 22 , ACS Catalysis , 4 6 , ACS Catalysis , 3 11 , The Journal of Physical Chemistry C , 28 , Hakim Siddiki, and Atsushi Satsuma. Sonawane, N. Rasal, S. Jagtap, Org. The methodology was also applied to urea and phthalimide to demonstrate its versatility and wide substrate scope.
A plausible mechanism explains the crucial role of water. Becerra-Figueroa , A. Ojeda-Porras, D. In the presence of a catalytic amount of L-proline, transamidations of carboxamides with amines were achieved under solvent-free conditions. The reaction tolerates a wide range of amines. Rao, D. Mohan, S. Admurthy, Org.
Nonplanar, electronically destabilized amides are powerful intermediates in organic synthesis. A highly selective method for transamidation of common secondary amides under mild, metal-free conditions relies on transient N-selective functionalization to weaken amidic resonance.
This procedure accomplishes challenging transamidation of secondary amides under mild conditions. Liu, S. Shi, M. Achtenhagen, R. Liu, M. Szostak, Org. Copper sulfate mediates a highly selective, mild, and rapid N-acylation of various aliphatic and aromatic amines using thioacids in methanol at neutral conditions.
All N-acylated products of primary and secondary amines were isolated in good yields. This method offers a simple workup, high yields, and is is not sensitive to other functional groups such as phenols, alcohols, and thiols.
Mali, R. Bhaisare, H. Gopi, J. A recently discovered precatalyst enables Pd-catalyzed Suzuki-Miyaura and Buchwald-Hartwig reactions involving cleavage of a C acyl -O bond of aryl esters as electrophiles under mild conditions. The Pd II precatalyst is highly active due to its fast reduction to a Pd 0 active species.
Dardir, P. Melvin, R. Davis, N. Hazari, M. Beromi, J. Krishnamurthy, T. Vishwanatha, N. Panguluri, V. Panduranga, V. Sureshbabu, Synlett, , 26, A tandem Lieben-Haller-Bauer reaction mechanism is proposed. Cao, J. Ding, M. Gao, Z. Li, A. Wu, Org. Talukdar, L. Saikia, A.
Thakur, Synlett, , An operationally straightforward method for the amidation of aldehydes with economic ammonium chloride or amine hydrochloride salts enables the synthesis of various amides in good yield by using inexpensive copper sulfate or copper I oxide as a catalyst and aqueous tert-butyl hydroperoxide as an oxidant. Chiral amines can be used without detectable racemization. Ghosh, J. Ngiam, A. Seayad, D. Tuan, C.
Chai, A. Chen, J. The use of diacetoxyiodobenzene in the presence of an ionic liquid enables a facile one-pot synthesis of a series of amides from aldehydes and amines at ambient temperature. Prasad, R. Kale, B. Mishra, D. Kumar, V. Tiwari, Org. A photoorganocatalytic reaction of aldehydes with diisopropyl azodicarboxylate leads to an intermediate carbonyl imide, which can react with a variety of amines to afford amides.
This method enables a mild, one-pot, and environmentally friendly synthesis of amides from aldehydes and amines. Papadopoulos, C. Kokotos, J. Using an efficient visible-light photocatalysis-based method, a mixture of an aldehyde, tert-butyl hydrogen peroxide, and N-chlorosuccinimide afforded an acid chloride in the presence of Ru bpy 3Cl2 as photocatalyst.
A subsequent reaction with an amine provided the corresponding amide. Iqbal, E. Cho, J. An oxidative amidation of aromatic aldehydes in the presence of low loadings of phenazine ethosulfate as an inexpensive metal-free visible light photocatalyst proceeds at ambient temperature and uses air as the sole oxidant. The operationally easy procedure provides an economical, green, and mild alternative for the formation of amide bonds.
Leow, Org. A general and efficient method enables the synthesis of tertiary amides from readily available tertiary amines and anhydrides in the presence of FeCl2 as catalyst and tert-butyl hydroperoxide in water T-Hydro as oxidant. Li, L. Ma, F. Jia, Z. Li, J. A novel oxygen-centered radical addition between acyl peroxides and isocyanides has been developed. A diverse collection of valuable arylcarboxyamides were easily synthesized by this protocol.
From the preliminary mechanistic study, the elimination of carbon dioxide affords the product via an intramolecular rearrangement. Chen, Y. Li, H. Tang, H. Ding, K. Wang, L. Li, M. Gao, A.
Lei, Org. TBPB is an efficient and highly chemoselective benzoylating reagent for aliphatic amines in the presence of aromatic amines and hydroxyl groups. Yadav, B. Bhanage, Synlett, , 26, Many types of amines are tolerant in this transformation. Wide substrate scope, and the use of air as oxidant and initiator make this transformation highly efficient and practical. Zhang, X. Zong, L. Zhang, N. Jiao, Org. The protocol is operationally straightforward and accomplished in good product yields and with complete chemoselectivity.
Ton, C. Tejo, S. Tania, J. Chang, P. Chan, J. A Co-catalyzed oxidant-free reaction of carboxylic acids with organic azides in the presence of tert-butyl isocyanide enables an effective synthesis of N-sulfonylcarboxamides in very good yields.
The protocol offers short times, low temperatures, and broad substrate scope. Fang, Z. Gu, S. Yang, S. Ji, J. N-Cbz-protected amino acids reacted with various aryl amines in the presence of methanesulfonyl chloride and N-methylimidazole in dichloromethane to give the corresponding arylamides in high yields without racemization under these mild conditions.
Mao, Z. Li, X. Han, W. Zhou, Synlett, , The rate acceleration is especially evident with traditionally unreactive, electron-deficient anilines.
DBU offers safety and cost advantages over more commonly employed catalysts such as 1-hydroxybenzotriazole HOBt. Larrive-Aboussafy, B.
Jones, K. Price, M. Hardink, R. McLaughlin, B. Lillie, J. Hawkins, R. Vaidyanathan, Org. Subsequent reactions with various nucleophiles in an efficient one-pot process leads to amides, esters or carboxylic acids. Lafrance, P. Bowles, K. Leeman, R. Rafka, Org. Deprotonated 1,2,4-triazole is an active acyl transfer catalyst suitable for the aminolysis and transesterification of esters.
Yang, V. Birman, Org. A N-heterocyclic carbene catalyzes the oxidative esterification of various aldehydes in the presence of 3,3',5'5-tetra-tert-butyldiphenoquinone to yield hexafluoroisopropylesters, which are useful active esters for in situ amide bond formation.
This transition metal-free organocatalytic system also enabled a mild oxidative azidation of aldehydes. De Sarkar, A. Studer, Org. Amines are efficiently acylated by both cyclic and acyclic anhydrides in aqueous medium with sodium dodecyl sulfate SDS - without use of acidic or basic reagents. Various amines and anhydrides were reacted with equal ease.
Chemoselective acylation in the presence of phenols and thiols has been achieved. No chromatographic separation is required for isolation of the acylated products. Naik, G. Bhattacharjya, B. Talukdar, B. Patel, Eur. Various alcohols, thiols, phenols, and amines can be acetylated using acetic anhydride in the presence of catalytic quantity of silver triflate.
The method proceeds under mild conditions, does not involve cumbersome workup, and the resulting products are obtained in high yields within a reasonable time. Das, D. Chakraborty, Synthesis, , Phosphomolybdic acid PMA is a simple and efficient catalyst for the acetylation of structurally diverse alcohols, phenols, and amines.
In quinine this nitrogen is restricted to one configuration by the bridged ring system. The other stereogenic nitrogens are free to assume two pyramidal configurations, but these are in rapid equilibrium so that distinct stereoisomers reflecting these sites cannot be easily isolated.
It should be noted that structural factors may serve to permit the resolution of pyramidal chiral amines. Because of the molecule's bridged structure, the nitrogens have the same configuration and cannot undergo inversion. The chloro aziridine can invert, but requires a higher activation energy to do so, compared with larger heterocyclic amines.
It has in fact been resolved, and pure enantiomers isolated. An increase in angle strain in the sp2-hybridized planar transition state is responsible for the greater stability of the pyramidal configuration. To see these features Click on the Diagram. Of course, quaternary ammonium salts, such as that in muscarine, have a tetrahedral configuration that is incapable of inversion. With four different substituents, such a nitrogen would be a stable stereogenic center.
Kim, J. Gupta, Z. Teichert, K. The nomenclature of amines is complicated by the fact that several different nomenclature systems exist, and there is no clear preference for one over the others.
A general and efficient method enables the synthesis of tertiary amides from readily available tertiary amines and anhydrides in the presence of FeCl2 as catalyst and tert-butyl hydroperoxide in water T-Hydro as oxidant. Zhu, S.
An effective protocol for a waste-minimized, environmentally benign thermal condensation of carboxylic acids with amines has been identified. Tanaka, Org. Okamoto, F. Rao, X. In the presence of sodium acetate, the reaction between 2,2,6-trimethyl-4H-1,3-dioxinone and secondary or tertiary alcohols or primary or secondary amines could be carried out in refluxing tetrahydrofuran.
Kim, K. The protocol is valuable for the coupling of carboxylates for which the corresponding carboxylic acids or acyl chlorides are unstable. Zong, L. Zhang, N.
This method offers a simple workup, high yields, and is is not sensitive to other functional groups such as phenols, alcohols, and thiols. Choudry, S. Hall, J. Ojeda-Porras, D. A straightforward trimethylsilylation protocol activates a thiol acid for peptide bond formation at neutral pH using bistrimethylsilylacetamide BSA. The rate acceleration is especially evident with traditionally unreactive, electron-deficient anilines.
Schaack, H. Chemoselective formylation of a primary amine could be readily achieved in the presence of an unprotected primary alcohol. Gao, Z. It has in fact been resolved, and pure enantiomers isolated. Gabriel, M. Wu, Z.
The nomenclature of amines is complicated by the fact that several different nomenclature systems exist, and there is no clear preference for one over the others. Kumar, A. The effect of cyclopropene substituents on the rate of conversion is examined. Organometallics , 38 4 , Chemoselective acylation in the presence of phenols and thiols has been achieved.
European Journal of Inorganic Chemistry , 10 , Torsten Irrgang, Rhett Kempe.