Synthesis of amides

Name Reactions

Recent Literature

The use of monodentate ligands that possess a methyl group ortho to the phosphorus center allows the coupling of various aryl and heteroaryl chlorides with various amides in high yield. These ligands can prevent the formation of the κ²-amidate complexes and thereby generate more stable catalysts for the amination of aryl chlorides.
T. Ikawa, T. E. Barder, M. R. Biscoe, S. L. Buchwald, J. Am. Chem. Soc., 2007, 129, 13001-13007.

The Xantphos/Pd-catalyzed intermolecular coupling of aryl halides and amides displays good functional group compatibility, and the desired C-N bond forming process proceeds in good to excellent yields. The arylation of sulfonamides, oxazolidinones, and ureas was found to be highly dependent on reaction concentrations and catalyst loadings.
J. Yin, S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 6043-6048.

Microwave-assisted, palladium-catalyzed C-N bond-forming reactions with aryl/heteroaryl nonaflates and amines using soluble amine bases resulted in good to excellent yields of arylamines in short reaction times.
R. E Tundel, K. W. Anderson, S. L. Buchwald, J. Org. Chem., 2006, 71, 430-433.

The arylation of N-H and O-H containing compounds at room temperature with phenylboronic acids is promoted in the presence of cupric acetate and a tertiary amine. Substrates include phenols, amines, anilines, amides, imides, ureas, carbamates, and sulfonamides.
D. M. T. Chan, K. L. Monaco, R.-P. Wang, M. P. Winteres, Tetrahedron Lett., 1998, 39, 2933-2936.

Iridium-catalyzed allylation of potassium trifluoroacetamide or the highly reactive ammonia equivalent lithium di-tert-butyliminodicarboxylate forms a range of conveniently protected, primary, α-branched allylic amines in high yields, high branched-to-linear regioselectivities, and high enantiomeric excess.
M. J. Pouy, A. Leitner, D. J. Weix, S. Ueno, J. F. Hartwig, Org. Lett., 2007, 9, 3949-3952.

Catalysts generated from Pd₂(dba)₃ and biphenyl ligands efficiently promote the coupling of amides and carbamates with unactivated vinyl triflates and tosylates, to provide enamides in good to excellent yields.
M. C. Willis, G. N. Brace, I. P. Holmes, Synthesis, 2005, 3229-3234.

1,1,1-Tris(hydroxymethyl)ethane as a New, Efficient, and Versatile Tripod Ligand for Copper-Catalyzed Cross-Coupling Reactions of Aryl Iodides with Amides, Thiols, and Phenols
Y.-J. Chen, H.-H. Chen, Org. Lett., 2006, 8, 5609-5612.

A versatile and efficient copper-catalyzed amidation of vinyl bromides and iodides has been developed. The protocol, which uses a combination of copper iodide and N,N'-dimethyl ethylenediamine, tolerates substrates bearing ester, silyl ether, and amino groups.
L. Jiang, G. E. Job, A. Klapars, S. L. Buchwald, Org. Lett., 2003, 5, 3667-3669.

A mild, ruthenium-catalyzed anti-Markovnikov addition of secondary amides, anilides, lactames, ureas, bislactames, and carbamates to terminal alkynes has been developped. Two complementary protocols provide either the E or the Z isomers.
L. J. Goossen, J. E. Rauhaus, G. Deng, Angew. Chem. Int. Ed., 2005, 44, 4042-4045.

A copper-catalyzed direct N-alkynylation of amides has been developed leading to a facile entry for syntheses of chiral ynamides.
M. O. Frederick, J. A. Mulder, M. R. Tracey, R. P. Hsung, J. Huang, K. C. M. Kurtz, L. Shen, C. J. Douglas, J. Am. Chem. Soc., 2003, 125, 2368-2369.

A rhodium-catalyzed N-H and O-H insertion of amides and carboxylic acids with α-diazo-β-ketoesters gives different α-amido- and α-carboxylic-β-ketoesters in good yields. The reactions were performed under mild conditions with 1 mol% of catalyst.
S. Bertelsen, M. Nielsen, S. Bachmann, K. A. Jorgensen, Synthesis, 2005, 2234-2238.

A range of enol triflates can be coupled with amides, carbamates, and sulfonamides using palladium catalysis. This method allows the synthesis of enamides, which may not be readily available by other means.
D. J. Wallace, D. J. Klauber, C.-Y. Chen, R. P. Volante, Org. Lett., 2003, 5, 4749-4752.

Several amides were obtained in high yields by an efficient method from the corresponding imines which are readily prepared from aldehydes. This procedure involves the oxidation of aldimines with m-CPBA and BF₃·OEt₂. In this reaction, the product is strongly influenced by the electron releasing capacity of the aromatic substituent (Ar).
G. An, M. Kim, J. Y. Kim, H. Rhee, Tetrahedron Lett., 2003, 44, 2183-2186.

An intramolecular vinylation of various iodoenamides using CuI as the catalyst and N,N'-dimethylethylenediamine as the ligand led to five- to seven-membered lactams in moderate to excellent yields.
T. Hu, C. Li, Org. Lett., 2005, 7, 2035-2038.

A convenient and efficient iron-catalyzed aminobromination of alkenes has been developed using inexpensive FeCl₂ as the catalyst, amides/sulfonamides and NBS as the nitrogen and bromine sources, respectively, under mild conditions.
Z. Wang, Y. Zhang, H. Fu, Y. Jiang, Y. Zhao, Synlett, 2008, 2667-2668.