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

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

Keywords

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

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1055/s-1995-4094

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

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.",

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

author = "Yusubov, {M. S.} and Filimonov, {V. D.} and V. Vasilyeva and Chi, {K. W.}",

year = "1995",

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doi = "10.1055/s-1995-4094",

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T1 - Chemoselective oxidation of carbon-carbon double or triple bonds to 1,2-diketones with DMSO-based reagents

AU - Yusubov, M. S.

AU - Filimonov, V. D.

AU - Vasilyeva, V.

AU - Chi, K. W.

PY - 1995/1/1

Y1 - 1995/1/1

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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