Synthesis of amides

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Reactions including a hydrolysis step (or a rearrangement)

Aminocarbonylation

Name Reactions

Recent Literature

Borane-tetrahydrofuran complex or borane-methyl sulfide complex is used to generate triacyloxyboranes, which can be effectively reacted with various nucleophiles (alkylamines, arylamines, hydrazides, alcohols, phenols) at reflux in toluene to provide the corresponding amides and esters in excellent yield.
Z. Huang, J. R. Reilly, R. N. Buckle, Synlett, 2007, 1026-1030.

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.
S. Naik, G. Bhattacharjya, B. Talukdar, B. K. Patel, Eur. J. Org. Chem., 2004, 1254-1260.

Copper(II) tetrafluoroborate efficiently catalyzes acetylation of structurally diverse phenols, alcohols, thiols, and amines with stoichiometric amounts of Ac₂O under solvent-free conditions at room temperature. Acid-sensitive alcohols are smoothly acetylated without competitive side reactions.
A. K. Chakraborti, R. Gulhane, Shivani, Synthesis, 2004, 111-115.

2-Acyl-4,5-dichloropyridazin-3-ones served as stable, convenient and chemoselective N-acylating reagents for amines under neutral conditions.
Y.-J. Kang, H.-A Chung, J.-J. Kim, Y.-J. Yoon, Synthesis, 2002, 733-738.

The reaction of N,N-dialkylformamide dimethyl acetal with primary amides produces N'-acyl-N,N-dialkylformamidines as intermediates. In the presence of certain Lewis acid additives efficient acyl transfer occurs, providing new and useful methods for amide exchange such as transamidation.
T. A. Dineen, M. A. Zajac, A. G. Myers, J. Am. Chem. Soc., 2006, 128, 16406-16409.

Microwave reactions of primary and secondary amines with imidoylbenzotriazoles gave various polysubstituted amidines in good yields. Convenient preparations of a variety of amides and imidoylbenzotriazoles have also been developed using microwave irradiation under mild conditions and short reaction times.
A. R. Katritzky, C. Cai, S. K. Singh, J. Org. Chem., 2006, 71, 3375-3380.

Various alcohols, phenols, amines and thiols may easily be converted into acetate derivatives by treatment with acetic anhydride in the presence of acetonyltriphenylphosphonium bromide in good yields at room temperature. With the same precatalyst, both aliphatic and aromatic aldehydes can be transformed into the corresponding gem-diacetates under reflux conditions.
A. T. Khan, L. H. Choudry, S. Ghosh, Eur. J. Org. Chem., 2005, 2782-2787.

Acyl halide-methanol mixtures are efficient reagents for the one-pot transformation of t-butyl carbamates into amides. This transformation can be carried out in the presence of a benzyloxycarbonyl group.
A. Nazih, D. Heissler, Synthesis, 2002, 203-206.

An efficient dynamic kinetic resolution of amines combines a ruthenium-catalyzed racemization with a lipase-catalyzed resolution. A variety of primary amines were transformed into one enantiomer of the amide in high yield and high enantioselectivity.
J. Paetzold, J. E. Bäckvall, J. Am. Chem. Soc., 2005, 127, 17620-17621.

A practical procedure for an efficient dynamic kinetic resolution of primary amines employs a palladium nanocatalyst as racemization catalyst, a commercial lipase as resolution catalyst, and ethyl acetate or ethyl methoxyacetate as acyl donor. Various amines and one amino acid amide have been resolved with good yields and high enantiomeric excesses.
M.-J. Kim, W.-H. Kim, K. Han, Y. K. Choi, J. Park, Org. Lett., 2007, 9, 1157-1159.

A mild, versatile, copper-catalyzed three-component coupling of organoindium reagents with imines and acid chlorides provides α-substituted amides or N-protected amines in a single step with the sole byproduct being indium trichloride.
D. A. Black, B. A. Arndtsen, Org. Lett., 2006, 8, 1991-1993.

A mild, simple, and selective N-formylation of amines with formic acid in the presence of ZnO under solvent-free conditions gives products in excellent yields.
M. Hosseini-Sarvari, H. Sharghi, J. Org. Chem., 2006, 71, 6652-6654.

Various tertiary benzanilide derivatives were effectively synthesized in high yields from a broad range substituted benzoic acid and N-monoalkylated anilines using dichlorotriphenylphosphorane in chloroform. Allyl, Boc, MPM and the Z group were unaffected under these conditions.
I. Azumaya, T. Okamoto, F. Imabeppu, H. Takayanagi, Tetrahedron, 2003, 59, 2325-2331.

An amidation of unactivated esters with amino alcohols catalazyed by a stable nitrogen-heterocyclic carbene is described. The mechanism is discussed.
M. Movassaghi, M. A. Schmidt, Org. Lett., 2005, 7, 2373-2376.

A small library of α,β-unsaturated oxindoles was prepared by an efficient microwave-assisted one-pot sequence comprising an aromatic substitution followed by an ionic Horner-Wadsworth-Emmons olefination.
A. Teichert, K. Jantos, K. Harms, A. Studer, Org. Lett., 2004, 6, 3477-3480.

Various alcohols, amines and N-hydroxylamines gave corresponding formylated adducts in high yields by treatment with 2,2,2-trifluoroethyl formate (TFEF). Chemoselective formylation of a primary amine could be readily achieved in the presence of an unprotected primary alcohol.
D. R. Hill, C.-N. Hsiao, R. Kurukulasuriya, S. Wittenberger, Org. Lett., 2002, 4, 111-113.

Deoxo-Fluor is a versatile and mild reagent for acyl fluoride generation and subsequent one-flask amide coupling. The conversion of acids to amides and Weinreb amides and the use of Deoxo-Fluor as peptide-coupling reagent have been explored. Products were isolated after facile purification in good yields.
J. M. White, A. R. Tunoori, B. J. Turunen, G. I. Georg, J. Org. Chem., 2004, 69, 2573-2576.

A stereoconservative protection and deprotection method of amino and carboxyl groups includes the generation of N-Phthaloyl N'-alkyl secondary amides from N-phthaloyl amino acids by using a mixed anhydride method. These secondary amides have been transformed by thermal rearrangement of the intermediate nitrosoamides to esters with retention of configuration and excellent yields.
D. M. Shendage, R. Froehlich, G. Haufe, Org. Lett., 2004, 6, 3675-3678.

A mild and efficient oxidative amidation of aldehydes uses amine HCl salts and tert-butyl hydroperoxide as an oxidant in the presence of a copper catalyst.
W.-J. Yoo, C.-J. Li, J. Am. Chem. Soc., 2006, 128, 13064-13065.

Related	Reactions including a hydrolysis step (or a rearrangement)
	Aminocarbonylation