Two-step continuous flow synthesis of amide via oxidative amidation of methylarene

Tingting Shi; Zhimin Zhang; Yuhang Yang; Zhao Yang; Wei He; Chengkou Liu; Zheng Fang; Kai Guo

doi:10.1016/j.tet.2020.131044

Two-step continuous flow synthesis of amide via oxidative amidation of methylarene

Tingting Shi, Zhimin Zhang, Yuhang Yang, Zhao Yang, Wei He, Chengkou Liu, Zheng Fang, Kai Guo

COLLEGE OF BIOTECHNOLOGY AND PHARMACEUTICAL ENGINEERING

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

3 Scopus citations

Abstract

A green and efficient method for the synthesis of amides has been developed through oxidative amidation between methylarenes with amines in a two-step continuous flow system. This method integrates methylarene oxidation and amide formation into a single operation which is usually accomplished separately. Oxidation with tert-butyl hydroperoxide (TBHP) as “green” oxidant, the synthesis of amides under mild reaction conditions in continuous flow system and the utilization of methylarenes as starting material make this methodology novel and environment friendly. The practical value of this method is highlighted through the synthesis of high-profile pharmaceutical agents, acetylprocainamide.

Original language	English
Article number	131044
Journal	Tetrahedron
Volume	76
Issue number	13
DOIs	https://doi.org/10.1016/j.tet.2020.131044
State	Published - 27 Mar 2020

Keywords

Amides
Catalysts
Continuous flow system
Methylarenes
Oxidative amidation

Access to Document

10.1016/j.tet.2020.131044

Cite this

@article{ed2fc9eb1c6441d3820d63619051782e,

title = "Two-step continuous flow synthesis of amide via oxidative amidation of methylarene",

abstract = "A green and efficient method for the synthesis of amides has been developed through oxidative amidation between methylarenes with amines in a two-step continuous flow system. This method integrates methylarene oxidation and amide formation into a single operation which is usually accomplished separately. Oxidation with tert-butyl hydroperoxide (TBHP) as “green” oxidant, the synthesis of amides under mild reaction conditions in continuous flow system and the utilization of methylarenes as starting material make this methodology novel and environment friendly. The practical value of this method is highlighted through the synthesis of high-profile pharmaceutical agents, acetylprocainamide.",

keywords = "Amides, Catalysts, Continuous flow system, Methylarenes, Oxidative amidation",

author = "Tingting Shi and Zhimin Zhang and Yuhang Yang and Zhao Yang and Wei He and Chengkou Liu and Zheng Fang and Kai Guo",

note = "Publisher Copyright: {\textcopyright} 2020 Elsevier Ltd",

year = "2020",

month = mar,

day = "27",

doi = "10.1016/j.tet.2020.131044",

language = "英语",

volume = "76",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "13",

}

TY - JOUR

T1 - Two-step continuous flow synthesis of amide via oxidative amidation of methylarene

AU - Shi, Tingting

AU - Zhang, Zhimin

AU - Yang, Yuhang

AU - Yang, Zhao

AU - He, Wei

AU - Liu, Chengkou

AU - Fang, Zheng

AU - Guo, Kai

PY - 2020/3/27

Y1 - 2020/3/27

N2 - A green and efficient method for the synthesis of amides has been developed through oxidative amidation between methylarenes with amines in a two-step continuous flow system. This method integrates methylarene oxidation and amide formation into a single operation which is usually accomplished separately. Oxidation with tert-butyl hydroperoxide (TBHP) as “green” oxidant, the synthesis of amides under mild reaction conditions in continuous flow system and the utilization of methylarenes as starting material make this methodology novel and environment friendly. The practical value of this method is highlighted through the synthesis of high-profile pharmaceutical agents, acetylprocainamide.

AB - A green and efficient method for the synthesis of amides has been developed through oxidative amidation between methylarenes with amines in a two-step continuous flow system. This method integrates methylarene oxidation and amide formation into a single operation which is usually accomplished separately. Oxidation with tert-butyl hydroperoxide (TBHP) as “green” oxidant, the synthesis of amides under mild reaction conditions in continuous flow system and the utilization of methylarenes as starting material make this methodology novel and environment friendly. The practical value of this method is highlighted through the synthesis of high-profile pharmaceutical agents, acetylprocainamide.

KW - Amides

KW - Catalysts

KW - Continuous flow system

KW - Methylarenes

KW - Oxidative amidation

UR - http://www.scopus.com/inward/record.url?scp=85079846276&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2020.131044

DO - 10.1016/j.tet.2020.131044

M3 - 文章

AN - SCOPUS:85079846276

SN - 0040-4020

VL - 76

JO - Tetrahedron

JF - Tetrahedron

IS - 13

M1 - 131044

ER -

Two-step continuous flow synthesis of amide via oxidative amidation of methylarene

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this