An Efficient Method for the Preparation of N-Formamides using Propylphosphonic Anhydride (T3P®)

Abstract

The synthesis of N-formamides from aromatic amines and formic acid using propylphosphonic anhydride (T3P®) as a green coupling reagent is described. By using this method, aryl, heteroaryl and fluorinated aryl-containing formamides were synthesized in high yield and purity. The significant features of this method include easy work up, high purity and reduced toxicity of the reaction.

Metal-Free N-Formylation of Amines Using Carbohydrates as C1 Synthon via C–C Bond Cleavage

“…This is a known compound, and the spectroscopic data agree with the literature. 84 The crude product was purified by column chromatography on silica gel (EtOAc/hexane 1.5: 8.5) to give 3h as a light-brown colored solid; yield: 130 mg (93%). The compound is a mixture of rotamers and the data for the major rotamer are given.…”

Microwave-Assisted, Metal-Free, Chemoselective N-Formylation of Amines using 2-Formyl-1,3-dimethyl-1H-imidazol-3-ium Iodide and In Situ Synthesis of Benzimidazole and Isocyanides

“…Direct N -formylation of various amines can be achieved using different formylating reagents such as formic acetic anhydride, 16 formic acid in the presence of coupling reagents such as T3P 17 and DCC, 18 Weinreb formamide, 19 methanol, 20 formyloxyacetoxyphenylmethane (FAPM), 21 carbon monoxide, 22 carbon dioxide, 23 24 25 ammonium formate, 26 N -formylbenzotrizole, 27 and organic and inorganic catalysis. 28 29 30…”

“…11 Formamides play an important role in the fields of biochemistry and molecular biology, especially in the area of nucleotides and polynucleotides. [12][13][14][15] Direct N-formylation of various amines can be achieved using different formylating reagents such as formic acetic anhydride, 16 formic acid in the presence of coupling reagents such as T3P 17 and DCC, 18 Weinreb formamide, 19 methanol, 20 formyloxyacetoxyphenylmethane (FAPM), 21 carbon monoxide, 22 carbon dioxide, [23][24][25] ammonium formate, 26 N-formylbenzotrizole, 27 and organic and inorganic catalysis. [28][29][30] However, many of these methods have limitations such as long reaction times, harsh reaction conditions, low yields, expensive reagents, lack of selectivity or generality, and decrease in turnover number of the catalyst.…”