Chemoselective oxidation of carbon-carbon double or triple bonds to 1,2-diketones with DMSO-based reagents

M. S. Yusubov, V. D. Filimonov, V. Vasilyeva, K. W. Chi

Research output: Contribution to journal › Article

Abstract

HBr/DMSO selectively oxidizes the double bond in (E)-1-(2-phenylethenyl)-4-(phenylethynyl)benzene (1) to 1,2-diketone 2. However, 1₂/DMSO and PdCl₂/DMSO oxidize only the triple bond in 1 to 1,2-diketone 3. A similar trend of chemoselectivity is shown for the oxidation of (E)-1,4-diphenyl-1-buten-3-yne (6) with the DMSO-based reagents.

Original language	English
Pages (from-to)	1234-1236
Number of pages	3
Journal	Synthesis
Issue number	10
DOIs	https://doi.org/10.1055/s-1995-4094
Publication status	Published - 1 Jan 1995

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Keywords

1,2-diketone
chemoselective oxidation
DMSO-based reagents
double or triple bond
Pd(II) catalyst

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Cite this

Yusubov, M. S., Filimonov, V. D., Vasilyeva, V., & Chi, K. W. (1995). Chemoselective oxidation of carbon-carbon double or triple bonds to 1,2-diketones with DMSO-based reagents. Synthesis, (10), 1234-1236. https://doi.org/10.1055/s-1995-4094

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abstract = "HBr/DMSO selectively oxidizes the double bond in (E)-1-(2-phenylethenyl)-4-(phenylethynyl)benzene (1) to 1,2-diketone 2. However, 12/DMSO and PdCl2/DMSO oxidize only the triple bond in 1 to 1,2-diketone 3. A similar trend of chemoselectivity is shown for the oxidation of (E)-1,4-diphenyl-1-buten-3-yne (6) with the DMSO-based reagents.",

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AU - Yusubov, M. S.

AU - Filimonov, V. D.

AU - Vasilyeva, V.

AU - Chi, K. W.

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N2 - HBr/DMSO selectively oxidizes the double bond in (E)-1-(2-phenylethenyl)-4-(phenylethynyl)benzene (1) to 1,2-diketone 2. However, 12/DMSO and PdCl2/DMSO oxidize only the triple bond in 1 to 1,2-diketone 3. A similar trend of chemoselectivity is shown for the oxidation of (E)-1,4-diphenyl-1-buten-3-yne (6) with the DMSO-based reagents.

AB - HBr/DMSO selectively oxidizes the double bond in (E)-1-(2-phenylethenyl)-4-(phenylethynyl)benzene (1) to 1,2-diketone 2. However, 12/DMSO and PdCl2/DMSO oxidize only the triple bond in 1 to 1,2-diketone 3. A similar trend of chemoselectivity is shown for the oxidation of (E)-1,4-diphenyl-1-buten-3-yne (6) with the DMSO-based reagents.

KW - 1,2-diketone

KW - chemoselective oxidation

KW - DMSO-based reagents

KW - double or triple bond

KW - Pd(II) catalyst

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10.1055/s-1995-4094