Synergistic Catalysis of Se and Cu for the Activation of α-H of Methyl Ketones with Molecular Oxygen/Alcohol to Produce α-Keto Acetals†

Chao Chen; Zhicheng Cao; Xu Zhang; Yiming Li; Lei Yu; Xuefeng Jiang

doi:10.1002/cjoc.202000089

Synergistic Catalysis of Se and Cu for the Activation of α-H of Methyl Ketones with Molecular Oxygen/Alcohol to Produce α-Keto Acetals^†

Chao Chen
, Zhicheng Cao
, Xu Zhang
, Yiming Li
, Lei Yu^*
, Xuefeng Jiang^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

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

37 Scopus citations

Abstract

Selenium and copper synergistically catalyzed the oxidation/alkoxylation of methyl ketones to synthesize α-keto acetals directly. Using O₂ as oxidant and alcohol as solvent and alkoxylation reagent, the reaction is practical from industrial viewpoint. Mechanistic studies revealed that copper promoted the oxidation of organoselenium intermediates with O₂ to allow the key rearrangement and selenoxide syn-elimination regenerating the catalytically active organoselenium species.

Original language	English
Pages (from-to)	1045-1051
Number of pages	7
Journal	Chinese Journal of Chemistry
Volume	38
Issue number	10
DOIs	https://doi.org/10.1002/cjoc.202000089
State	Published - 1 Oct 2020

Keywords

Acetal
Copper
C—H activation
Ketone
Oxidation
Selenium

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10.1002/cjoc.202000089

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title = "Synergistic Catalysis of Se and Cu for the Activation of α-H of Methyl Ketones with Molecular Oxygen/Alcohol to Produce α-Keto Acetals†",

abstract = "Selenium and copper synergistically catalyzed the oxidation/alkoxylation of methyl ketones to synthesize α-keto acetals directly. Using O2 as oxidant and alcohol as solvent and alkoxylation reagent, the reaction is practical from industrial viewpoint. Mechanistic studies revealed that copper promoted the oxidation of organoselenium intermediates with O2 to allow the key rearrangement and selenoxide syn-elimination regenerating the catalytically active organoselenium species.",

keywords = "Acetal, Copper, C—H activation, Ketone, Oxidation, Selenium",

author = "Chao Chen and Zhicheng Cao and Xu Zhang and Yiming Li and Lei Yu and Xuefeng Jiang",

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year = "2020",

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T1 - Synergistic Catalysis of Se and Cu for the Activation of α-H of Methyl Ketones with Molecular Oxygen/Alcohol to Produce α-Keto Acetals†

AU - Chen, Chao

AU - Cao, Zhicheng

AU - Zhang, Xu

AU - Li, Yiming

AU - Yu, Lei

AU - Jiang, Xuefeng

PY - 2020/10/1

Y1 - 2020/10/1

N2 - Selenium and copper synergistically catalyzed the oxidation/alkoxylation of methyl ketones to synthesize α-keto acetals directly. Using O2 as oxidant and alcohol as solvent and alkoxylation reagent, the reaction is practical from industrial viewpoint. Mechanistic studies revealed that copper promoted the oxidation of organoselenium intermediates with O2 to allow the key rearrangement and selenoxide syn-elimination regenerating the catalytically active organoselenium species.

AB - Selenium and copper synergistically catalyzed the oxidation/alkoxylation of methyl ketones to synthesize α-keto acetals directly. Using O2 as oxidant and alcohol as solvent and alkoxylation reagent, the reaction is practical from industrial viewpoint. Mechanistic studies revealed that copper promoted the oxidation of organoselenium intermediates with O2 to allow the key rearrangement and selenoxide syn-elimination regenerating the catalytically active organoselenium species.

KW - Acetal

KW - Copper

KW - C—H activation

KW - Ketone

KW - Oxidation

KW - Selenium

UR - https://www.scopus.com/pages/publications/85086449223

U2 - 10.1002/cjoc.202000089

DO - 10.1002/cjoc.202000089

M3 - 文章

AN - SCOPUS:85086449223

SN - 1001-604X

VL - 38

SP - 1045

EP - 1051

JO - Chinese Journal of Chemistry

JF - Chinese Journal of Chemistry

IS - 10

ER -

Synergistic Catalysis of Se and Cu for the Activation of α-H of Methyl Ketones with Molecular Oxygen/Alcohol to Produce α-Keto Acetals^†

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Keywords

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