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Synthesis of Tertiary Aromatic Amides from Tertiary Benzylamines via TBAI/TBHP‐Mediated C‐N‐Bond Cleavage
Author(s) -
Dai Feiyang,
Yang Yuhang,
Gu Jiajia,
Fang Zheng,
Yang Zhao,
Liu Chengkou,
He Wei,
Zhu Ning,
Lu Bushi,
Guo Kai
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201900090
Subject(s) - benzaldehyde , tertiary amine , chemistry , amide , amine gas treating , cleavage (geology) , bond cleavage , tertiary alcohols , organic chemistry , combinatorial chemistry , medicinal chemistry , catalysis , materials science , fracture (geology) , composite material
A novel method of the synthesis of tertiary aromatic amides from tertiary benzylamines with high atom utilization has been developed. The reaction undergoes a different mechanism, which is divided into two parts: firstly tertiary amine is decomposed (into benzaldehyde and secondary amine) via TBAI/TBHP–mediated C−N bond cleavage, then tertiary amide is generated through the oxidative amidation of the intermediates products (benzaldehyde and secondary amine). These two parts of reaction are integrated into a single operation, which provides moderate to excellent yields with a wide suabstrate scope.