Evidence of Cu I /Cu II Redox Process by X‐ray Absorption and EPR Spectroscopy: Direct Synthesis of Dihydrofurans from β‐Ketocarbonyl Derivatives and Olefins
The Cu I /Cu II and Cu I /Cu III catalytic cycles have been subject to intense debate in the field of copper‐catalyzed oxidative coupling reactions. A mechanistic study on the Cu I /Cu II redox process, by X‐ray absorption (XAS) and electron paramagnetic resonance (EPR) spectroscopies, has elucidate...
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| Published in | Chemistry : a European journal Vol. 21; no. 52; pp. 18925 - 18929 |
|---|---|
| Main Authors | , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WEINHEIM
Wiley
21.12.2015
Wiley Blackwell (John Wiley & Sons) |
| Subjects | |
| Online Access | Get full text |
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| Abstract | The Cu
I
/Cu
II
and Cu
I
/Cu
III
catalytic cycles have been subject to intense debate in the field of copper‐catalyzed oxidative coupling reactions. A mechanistic study on the Cu
I
/Cu
II
redox process, by X‐ray absorption (XAS) and electron paramagnetic resonance (EPR) spectroscopies, has elucidated the reduction mechanism of Cu
II
to Cu
I
by 1,3‐diketone and detailed investigation revealed that the halide ion is important for the reduction process. The oxidative nature of the thereby‐formed Cu
I
has also been studied by XAS and EPR spectroscopy. This mechanistic information is applicable to the copper‐catalyzed oxidative cyclization of β‐ketocarbonyl derivatives to dihydrofurans. This protocol provides an ideal route to highly substituted dihydrofuran rings from easily available 1,3‐dicarbonyls and olefins. |
|---|---|
| AbstractList | Abstract
The Cu
I
/Cu
II
and Cu
I
/Cu
III
catalytic cycles have been subject to intense debate in the field of copper‐catalyzed oxidative coupling reactions. A mechanistic study on the Cu
I
/Cu
II
redox process, by X‐ray absorption (XAS) and electron paramagnetic resonance (EPR) spectroscopies, has elucidated the reduction mechanism of Cu
II
to Cu
I
by 1,3‐diketone and detailed investigation revealed that the halide ion is important for the reduction process. The oxidative nature of the thereby‐formed Cu
I
has also been studied by XAS and EPR spectroscopy. This mechanistic information is applicable to the copper‐catalyzed oxidative cyclization of β‐ketocarbonyl derivatives to dihydrofurans. This protocol provides an ideal route to highly substituted dihydrofuran rings from easily available 1,3‐dicarbonyls and olefins. The Cu-I/Cu-II and Cu-I/Cu-III catalytic cycles have been subject to intense debate in the field of copper-catalyzed oxidative coupling reactions. A mechanistic study on the Cu-I/Cu-II redox process, by X-ray absorption (XAS) and electron paramagnetic resonance (EPR) spectroscopies, has elucidated the reduction mechanism of Cu-II to Cu-I by 1,3-diketone and detailed investigation revealed that the halide ion is important for the reduction process. The oxidative nature of the thereby-formed Cu-I has also been studied by XAS and EPR spectroscopy. This mechanistic information is applicable to the copper-catalyzed oxidative cyclization of beta-ketocarbonyl derivatives to dihydrofurans. This protocol provides an ideal route to highly substituted dihydrofuran rings from easily available 1,3-dicarbonyls and olefins. The Cu I /Cu II and Cu I /Cu III catalytic cycles have been subject to intense debate in the field of copper‐catalyzed oxidative coupling reactions. A mechanistic study on the Cu I /Cu II redox process, by X‐ray absorption (XAS) and electron paramagnetic resonance (EPR) spectroscopies, has elucidated the reduction mechanism of Cu II to Cu I by 1,3‐diketone and detailed investigation revealed that the halide ion is important for the reduction process. The oxidative nature of the thereby‐formed Cu I has also been studied by XAS and EPR spectroscopy. This mechanistic information is applicable to the copper‐catalyzed oxidative cyclization of β‐ketocarbonyl derivatives to dihydrofurans. This protocol provides an ideal route to highly substituted dihydrofuran rings from easily available 1,3‐dicarbonyls and olefins. |
| Author | Fan, Chao Yi, Hong Zhang, Xu Bunel, Emilio E. Lee, Jyh‐Fu Zhang, Guanghui Liao, Zhixiong Pao, Chih‐Wen Zhang, Guoting Lei, Aiwen |
| Author_xml | – sequence: 1 givenname: Hong surname: Yi fullname: Yi, Hong – sequence: 2 givenname: Zhixiong surname: Liao fullname: Liao, Zhixiong – sequence: 3 givenname: Guanghui surname: Zhang fullname: Zhang, Guanghui – sequence: 4 givenname: Guoting surname: Zhang fullname: Zhang, Guoting – sequence: 5 givenname: Chao surname: Fan fullname: Fan, Chao – sequence: 6 givenname: Xu surname: Zhang fullname: Zhang, Xu – sequence: 7 givenname: Emilio E. surname: Bunel fullname: Bunel, Emilio E. – sequence: 8 givenname: Chih‐Wen surname: Pao fullname: Pao, Chih‐Wen – sequence: 9 givenname: Jyh‐Fu surname: Lee fullname: Lee, Jyh‐Fu – sequence: 10 givenname: Aiwen surname: Lei fullname: Lei, Aiwen |
| BackLink | https://www.osti.gov/biblio/1786152$$D View this record in Osti.gov |
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| Keywords | OXIDATION CU(I) COMPLEXES BOND FORMATION OPERANDO IR redox chemistry FUNCTIONALIZATION oxidative coupling AMINATION homogeneous catalysis COUPLING REACTION ARYL HALIDES copper FREE-RADICAL REACTIONS X-ray absorption spectroscopy |
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| Snippet | The Cu
I
/Cu
II
and Cu
I
/Cu
III
catalytic cycles have been subject to intense debate in the field of copper‐catalyzed oxidative coupling reactions. A... The Cu-I/Cu-II and Cu-I/Cu-III catalytic cycles have been subject to intense debate in the field of copper-catalyzed oxidative coupling reactions. A... Abstract The Cu I /Cu II and Cu I /Cu III catalytic cycles have been subject to intense debate in the field of copper‐catalyzed oxidative coupling reactions. A... |
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| SubjectTerms | Chemistry Chemistry, Multidisciplinary Physical Sciences Science & Technology |
| Title | Evidence of Cu I /Cu II Redox Process by X‐ray Absorption and EPR Spectroscopy: Direct Synthesis of Dihydrofurans from β‐Ketocarbonyl Derivatives and Olefins |
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