Cu-Catalyzed aerobic oxidative cleavage of C(sp3)–C(sp3) bond: Synthesis of α-ketoamides

Jingming Zhang; Chengkou Liu; Man Yang; Zheng Fang; Kai Guo

doi:10.1016/j.tetlet.2020.152555

Cu-Catalyzed aerobic oxidative cleavage of C(sp3)–C(sp3) bond: Synthesis of α-ketoamides

Jingming Zhang, Chengkou Liu, Man Yang, Zheng Fang, Kai Guo

COLLEGE OF BIOTECHNOLOGY AND PHARMACEUTICAL ENGINEERING

Nanjing Tech University

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

8 Scopus citations

Abstract

A novel synthesis of α-ketoamides from Cu-catalyzed aerobic oxidative C(sp3)–C(sp3) bond cleavage of hydrocinnamaldehydes has been developed. Readily available and environmentally benign oxygen is used as the oxidant. This reaction avoids the use of noble metal catalysts or specialized oxidants, and chemoselectively yields α-ketoamide. Moreover, based on various control experiments, a reasonable mechanism is proposed.

Original language	English
Article number	152555
Journal	Tetrahedron Letters
Volume	61
Issue number	47
DOIs	https://doi.org/10.1016/j.tetlet.2020.152555
State	Published - 19 Nov 2020

Keywords

Copper catalyst
Hydrocinnamaldehyde
Oxidative cleavage
Oxygen
α-Ketoamide

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title = "Cu-Catalyzed aerobic oxidative cleavage of C(sp3)–C(sp3) bond: Synthesis of α-ketoamides",

abstract = "A novel synthesis of α-ketoamides from Cu-catalyzed aerobic oxidative C(sp3)–C(sp3) bond cleavage of hydrocinnamaldehydes has been developed. Readily available and environmentally benign oxygen is used as the oxidant. This reaction avoids the use of noble metal catalysts or specialized oxidants, and chemoselectively yields α-ketoamide. Moreover, based on various control experiments, a reasonable mechanism is proposed.",

keywords = "Copper catalyst, Hydrocinnamaldehyde, Oxidative cleavage, Oxygen, α-Ketoamide",

author = "Jingming Zhang and Chengkou Liu and Man Yang and Zheng Fang and Kai Guo",

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T2 - Synthesis of α-ketoamides

AU - Zhang, Jingming

AU - Liu, Chengkou

AU - Yang, Man

AU - Fang, Zheng

AU - Guo, Kai

PY - 2020/11/19

Y1 - 2020/11/19

N2 - A novel synthesis of α-ketoamides from Cu-catalyzed aerobic oxidative C(sp3)–C(sp3) bond cleavage of hydrocinnamaldehydes has been developed. Readily available and environmentally benign oxygen is used as the oxidant. This reaction avoids the use of noble metal catalysts or specialized oxidants, and chemoselectively yields α-ketoamide. Moreover, based on various control experiments, a reasonable mechanism is proposed.

AB - A novel synthesis of α-ketoamides from Cu-catalyzed aerobic oxidative C(sp3)–C(sp3) bond cleavage of hydrocinnamaldehydes has been developed. Readily available and environmentally benign oxygen is used as the oxidant. This reaction avoids the use of noble metal catalysts or specialized oxidants, and chemoselectively yields α-ketoamide. Moreover, based on various control experiments, a reasonable mechanism is proposed.

KW - Copper catalyst

KW - Hydrocinnamaldehyde

KW - Oxidative cleavage

KW - Oxygen

KW - α-Ketoamide

UR - http://www.scopus.com/inward/record.url?scp=85094612198&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2020.152555

DO - 10.1016/j.tetlet.2020.152555

M3 - 文章

AN - SCOPUS:85094612198

SN - 0040-4039

VL - 61

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 47

M1 - 152555

ER -

Cu-Catalyzed aerobic oxidative cleavage of C(sp3)–C(sp3) bond: Synthesis of α-ketoamides

Abstract

Keywords

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