High-load, soluble oligomeric carbodiimide: synthesis and application in coupling reactions.
A facile preparation of a high-load, soluble oligomeric alkyl cyclohexylcarbodiimide (OACC) reagent via ROM polymerization from commercially available starting materials is described. This reagent is exploited as a coupling reagent for esterification, amidation, and dehydration of carboxylic acids (aliphatic and aromatic) with an assortment of alcohols (aliphatic primary, secondary, and benzylic), thiols, phenols, and amines (aliphatic primary, secondary, benzylic, and aromatic/anilines), respectively. Following the coupling event, precipitation with an appropriate solvent (Et(2)O, MeOH, or EtOAc), followed by filtration through a SPE provides the products in good to excellent yield and purity.
Zhang
Mianji
M
Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, USA.
Vedantham
Punitha
P
Flynn
Daniel L
DL
Hanson
Paul R
PR
D002234:Carbodiimides / Q000138:chemical synthesis* / Q000737:chemistry*; D008968:Molecular Conformation
D002234:Carbodiimides