Direct syntheses of styryl ethers from benzyl alcohols via ag nanoparticle-catalyzed tandem aerobic oxidation

Qi Zhang; Shuangfei Cai; Linsen Li; Yifeng Chen; Hongpan Rong; Zhiqiang Niu; Junjia Liu; Wei He; Yadong Li

doi:10.1021/cs400295h

Direct syntheses of styryl ethers from benzyl alcohols via ag nanoparticle-catalyzed tandem aerobic oxidation

Qi Zhang, Shuangfei Cai, Linsen Li, Yifeng Chen, Hongpan Rong, Zhiqiang Niu, Junjia Liu, Wei He^*, Yadong Li

^*Corresponding author for this work

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

32 Citations (Scopus)

Abstract

Ag nanoparticle-catalyzed aerobic oxidation of benzyl alcohols in basic DMSO gave efficient formation of styryl ethers, featuring single carbon transfer and Cî - C and C-O bond formation. A deuterium labeling experiment established that DMSO was the carbon source. Further experiments showed the reaction proceeded through a styryl sulfoxide intermediate originating from basic DMSO and transient benzaldehyde. Control reactions in the absence of the Ag NPs or air indicated that oxidation of the styryl sulfoxide was required for the final C-O bond formation. This work demonstrated that metal nanoparticles could be applied to tandem heterogeneous catalysis in organic chemistry.

Original language	English
Pages (from-to)	1681-1684
Number of pages	4
Journal	ACS Catalysis
Volume	3
Issue number	7
DOIs	https://doi.org/10.1021/cs400295h
Publication status	Published - 5 Jul 2013
Externally published	Yes

Keywords

Ag nanoparticle
aerobic oxidation
styryl ether
tandem catalysis

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10.1021/cs400295h

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title = "Direct syntheses of styryl ethers from benzyl alcohols via ag nanoparticle-catalyzed tandem aerobic oxidation",

abstract = "Ag nanoparticle-catalyzed aerobic oxidation of benzyl alcohols in basic DMSO gave efficient formation of styryl ethers, featuring single carbon transfer and C{\^i} - C and C-O bond formation. A deuterium labeling experiment established that DMSO was the carbon source. Further experiments showed the reaction proceeded through a styryl sulfoxide intermediate originating from basic DMSO and transient benzaldehyde. Control reactions in the absence of the Ag NPs or air indicated that oxidation of the styryl sulfoxide was required for the final C-O bond formation. This work demonstrated that metal nanoparticles could be applied to tandem heterogeneous catalysis in organic chemistry.",

keywords = "Ag nanoparticle, aerobic oxidation, styryl ether, tandem catalysis",

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T1 - Direct syntheses of styryl ethers from benzyl alcohols via ag nanoparticle-catalyzed tandem aerobic oxidation

AU - Zhang, Qi

AU - Cai, Shuangfei

AU - Li, Linsen

AU - Chen, Yifeng

AU - Rong, Hongpan

AU - Niu, Zhiqiang

AU - Liu, Junjia

AU - He, Wei

AU - Li, Yadong

PY - 2013/7/5

Y1 - 2013/7/5

N2 - Ag nanoparticle-catalyzed aerobic oxidation of benzyl alcohols in basic DMSO gave efficient formation of styryl ethers, featuring single carbon transfer and Cî - C and C-O bond formation. A deuterium labeling experiment established that DMSO was the carbon source. Further experiments showed the reaction proceeded through a styryl sulfoxide intermediate originating from basic DMSO and transient benzaldehyde. Control reactions in the absence of the Ag NPs or air indicated that oxidation of the styryl sulfoxide was required for the final C-O bond formation. This work demonstrated that metal nanoparticles could be applied to tandem heterogeneous catalysis in organic chemistry.

AB - Ag nanoparticle-catalyzed aerobic oxidation of benzyl alcohols in basic DMSO gave efficient formation of styryl ethers, featuring single carbon transfer and Cî - C and C-O bond formation. A deuterium labeling experiment established that DMSO was the carbon source. Further experiments showed the reaction proceeded through a styryl sulfoxide intermediate originating from basic DMSO and transient benzaldehyde. Control reactions in the absence of the Ag NPs or air indicated that oxidation of the styryl sulfoxide was required for the final C-O bond formation. This work demonstrated that metal nanoparticles could be applied to tandem heterogeneous catalysis in organic chemistry.

KW - Ag nanoparticle

KW - aerobic oxidation

KW - styryl ether

KW - tandem catalysis

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DO - 10.1021/cs400295h

M3 - Article

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SP - 1681

EP - 1684

JO - ACS Catalysis

JF - ACS Catalysis

IS - 7

ER -

Direct syntheses of styryl ethers from benzyl alcohols via ag nanoparticle-catalyzed tandem aerobic oxidation

Abstract

Keywords

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