Anodic coupling of carboxylic acids to electron-rich double bonds: A surprising non-Kolbe pathway to lactones

Robert J. Perkins; Hai Chao Xu; John M. Campbell; Kevin D. Moeller

doi:10.3762/bjoc.9.186

Anodic coupling of carboxylic acids to electron-rich double bonds: A surprising non-Kolbe pathway to lactones

Robert J. Perkins, Hai Chao Xu, John M. Campbell, Kevin D. Moeller

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

36 Scopus citations

Abstract

Carboxylic acids have been electro-oxidatively coupled to electron-rich olefins to form lactones. Kolbe decarboxylation does not appear to be a significant competing pathway. Experimental results indicate that oxidation occurs at the olefin and that the reaction proceeds through a radical cation intermediate.

Original language	English
Pages (from-to)	1630-1636
Number of pages	7
Journal	Beilstein Journal of Organic Chemistry
Volume	9
DOIs	https://doi.org/10.3762/bjoc.9.186
State	Published - Aug 9 2013

Keywords

Carboxylic acid
Cyclization
Electrolysis
Free radical
Kolbe
Radical cation

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10.3762/bjoc.9.186

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title = "Anodic coupling of carboxylic acids to electron-rich double bonds: A surprising non-Kolbe pathway to lactones",

abstract = "Carboxylic acids have been electro-oxidatively coupled to electron-rich olefins to form lactones. Kolbe decarboxylation does not appear to be a significant competing pathway. Experimental results indicate that oxidation occurs at the olefin and that the reaction proceeds through a radical cation intermediate.",

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AU - Perkins, Robert J.

AU - Xu, Hai Chao

AU - Campbell, John M.

AU - Moeller, Kevin D.

PY - 2013/8/9

Y1 - 2013/8/9

N2 - Carboxylic acids have been electro-oxidatively coupled to electron-rich olefins to form lactones. Kolbe decarboxylation does not appear to be a significant competing pathway. Experimental results indicate that oxidation occurs at the olefin and that the reaction proceeds through a radical cation intermediate.

AB - Carboxylic acids have been electro-oxidatively coupled to electron-rich olefins to form lactones. Kolbe decarboxylation does not appear to be a significant competing pathway. Experimental results indicate that oxidation occurs at the olefin and that the reaction proceeds through a radical cation intermediate.

KW - Carboxylic acid

KW - Cyclization

KW - Electrolysis

KW - Free radical

KW - Kolbe

KW - Radical cation

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M3 - Article

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JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

Anodic coupling of carboxylic acids to electron-rich double bonds: A surprising non-Kolbe pathway to lactones

Abstract

Keywords

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