Synthesis of Tertiary Aromatic Amides from Tertiary Benzylamines via TBAI/TBHP-Mediated C-N-Bond Cleavage

Feiyang Dai; Yuhang Yang; Jiajia Gu; Zheng Fang; Zhao Yang; Chengkou Liu; Wei He; Ning Zhu; Bushi Lu; Kai Guo

doi:10.1002/slct.201900090

Synthesis of Tertiary Aromatic Amides from Tertiary Benzylamines via TBAI/TBHP-Mediated C-N-Bond Cleavage

Feiyang Dai, Yuhang Yang, Jiajia Gu, Zheng Fang, Zhao Yang, Chengkou Liu, Wei He, Ning Zhu, Bushi Lu, Kai Guo

COLLEGE OF BIOTECHNOLOGY AND PHARMACEUTICAL ENGINEERING

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	3500-3504
Number of pages	5
Journal	ChemistrySelect
Volume	4
Issue number	12
DOIs	https://doi.org/10.1002/slct.201900090
State	Published - 29 Mar 2019

Keywords

Amide
Catalysts
C−N bond cleavage
Synthesis

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10.1002/slct.201900090

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abstract = "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.",

keywords = "Amide, Catalysts, C−N bond cleavage, Synthesis",

author = "Feiyang Dai and Yuhang Yang and Jiajia Gu and Zheng Fang and Zhao Yang and Chengkou Liu and Wei He and Ning Zhu and Bushi Lu and Kai Guo",

note = "Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2019",

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doi = "10.1002/slct.201900090",

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T1 - Synthesis of Tertiary Aromatic Amides from Tertiary Benzylamines via TBAI/TBHP-Mediated C-N-Bond Cleavage

AU - Dai, Feiyang

AU - Yang, Yuhang

AU - Gu, Jiajia

AU - Fang, Zheng

AU - Yang, Zhao

AU - Liu, Chengkou

AU - He, Wei

AU - Zhu, Ning

AU - Lu, Bushi

AU - Guo, Kai

PY - 2019/3/29

Y1 - 2019/3/29

N2 - 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.

AB - 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.

KW - Amide

KW - Catalysts

KW - C−N bond cleavage

KW - Synthesis

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DO - 10.1002/slct.201900090

M3 - 文章

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SN - 2365-6549

VL - 4

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JO - ChemistrySelect

JF - ChemistrySelect

IS - 12

ER -

Synthesis of Tertiary Aromatic Amides from Tertiary Benzylamines via TBAI/TBHP-Mediated C-N-Bond Cleavage

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Keywords

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