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Facile amidation of esters with aromatic amines promoted by lanthanide tris (amide) complexes
Author(s) -
Li Zhao,
Guo Chenjun,
Chen Jue,
Yao Yingming,
Luo Yunjie
Publication year - 2020
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.5517
Subject(s) - chemistry , amide , amine gas treating , tris , lanthanide , catalysis , substrate (aquarium) , nucleophile , organic chemistry , combinatorial chemistry , ion , biochemistry , oceanography , geology
The development of catalysts capable of catalyzing amidation of esters with amines to construct amides under mild conditions is of great importance. Compared to aliphatic amines, the direct catalytic amidation of esters with less nucleophilic aromatic amines is rather difficult. Employing simple lanthanide tris (amide) complexes Ln[N (SiMe 3 ) 2 ] 3 ( μ ‐Cl)Li (THF) 3 as the catalysts, it was found a broad range of aromatic amines and esters were efficiently converted into various amides in good yields under mild conditions. A plausible mechanism for this transformation was experimentally supported as starting from an amide exchange reaction between the lanthanide tris (amide) complex and the substrate amine.