Recyclable hypervalent iodine(III) reagent iodosodilactone as an efficient coupling reagent for direct esterification, amidation, and peptide coupling.
A hypervalent iodine(III) reagent plays a novel role as an efficient coupling reagent to promote the direct condensation between carboxylic acids and alcohols or amines to provide esters, macrocyclic lactones, amides, as well as peptides without racemization. The regeneration of iodosodilactone (1) can also be readily achieved. The intermediate acyloxyphosphonium ion C from the activation of a carboxylic acid is thought to be involved in the present esterification reaction.
State Key Laboratory of Elemento-Organic Chemistry, The Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, PR of China.
Jun
J
Tian
Wen-Chao
WC
Gao
Dong-Mei
DM
Zhou
Chi
C
Zhang
D000586:Amination; D002264:Carboxylic Acids / Q000737:chemistry; D004951:Esterification; D007455:Iodine / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*
D002264:Carboxylic Acids; D007783:Lactones; D010455:Peptides; D007455:Iodine