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Metal‐Free Synthesis of N ‐Aryl Amides using Organocatalytic Ring‐Opening Aminolysis of Lactones
Author(s) -
Guo Wusheng,
Gómez José Enrique,
MartínezRodríguez Luis,
Bandeira Nuno A. G.,
Bo Carles,
Kleij Arjan W.
Publication year - 2017
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201700415
Subject(s) - aminolysis , chemistry , amide , aryl , catalysis , ring (chemistry) , combinatorial chemistry , atom economy , organic chemistry , organocatalysis , molecule , primary (astronomy) , enantioselective synthesis , alkyl , physics , astronomy
Catalytic ring‐opening of bio‐sourced non‐strained lactones with aromatic amines can offer a straightforward, 100 % atom‐economical, and sustainable pathway towards relevant N ‐aryl amide scaffolds. Herein, the first general, metal‐free, and highly efficient N ‐aryl amide formation is reported from poorly reactive aromatic amines and non‐strained lactones under mild operating conditions using an organic bicyclic guanidine catalyst. This protocol has high application potential as exemplified by the formal syntheses of drug‐relevant molecules.