Iodine and Brønsted acid catalyzed C–C bond cleavage of 1,3-diketones for the acylation of amines

Abstract

A metal-free N-acylation method of anilines with 1,3-diketones has been developed, by using iodine and p-toluene sulfonic acid as the co-catalysts. The reaction can proceed in 1,4-dioxane at elevated temperature to produce the corresponding amides with 48–89% yields. Further, the gram-scale experiment was carried out under the standard conditions and the possible mechanism was proposed.

Graphical Abstract

Keywords:

• Acylation
• amine
• 1,3-diketones
• iodine
• p-toluene sulfonic acid

Additional information

Funding

The work was supported by the Science and Technology Foundation Project of Guizhou Province [Grant No. qiankehejichu (2018) number 1141], the Science and Technology Foundation Project of Liupanshui [Grant No. 52020-2018-04-10] and the Science and Technology Foundation Project of Guizhou Province [Grant No. qiankehe LH zi (2014) number 7450].