One‐pot multistep electrochemical strategy for the modular synthesis of epoxides, glycols, and aldehydes from alkenes
Abstract Oxidative functionalization of alkenes is a versatile strategy for the preparation of many oxygen‐containing scaffolds, such as epoxides, diols, or carbonyl‐containing compounds. In addition to conventional chemical methods, which rely on the utilization of stoichiometric amounts of oxidizi...
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Wiley-VCH
2021-08-01
|
| Series: | Electrochemical Science Advances |
| Subjects: | |
| Online Access: | https://doi.org/10.1002/elsa.202100002 |
| _version_ | 1818363255604641792 |
|---|---|
| author | Wolfgang Jud C. Oliver Kappe David Cantillo |
| author_facet | Wolfgang Jud C. Oliver Kappe David Cantillo |
| author_sort | Wolfgang Jud |
| collection | DOAJ |
| description | Abstract Oxidative functionalization of alkenes is a versatile strategy for the preparation of many oxygen‐containing scaffolds, such as epoxides, diols, or carbonyl‐containing compounds. In addition to conventional chemical methods, which rely on the utilization of stoichiometric amounts of oxidizing reagents, some electrochemical procedures have been developed to achieve these transformations. Typical electrochemical procedures employ tailored and often complex redox mediators to achieve the target transformation. Herein we present a modular approach for the synthesis of epoxides, diols, and aldehydes from a single set of reaction components. With sodium bromide as an inexpensive electrocatalyst and water as the oxygen donor, the outcome of the reaction (epoxide, 1,2‐diol, or aldehyde) can be selected by simply tuning the electrolysis conditions. This convenient platform has been accomplished by developing a selective one‐pot three‐step bromide‐electrocatalyzed epoxidation/ring opening/carbon‐carbon cleavage sequence. Its modularity permits the selection of the desired product, as the sequential reaction can be ended when the target compound has been formed. The method has been applied to a diversely functionalized terminal and non‐terminal olefins. |
| first_indexed | 2024-12-13T21:45:34Z |
| format | Article |
| id | doaj.art-a3e87d3ba77345cba7c02074bd759547 |
| institution | Directory Open Access Journal |
| issn | 2698-5977 |
| language | English |
| last_indexed | 2024-12-13T21:45:34Z |
| publishDate | 2021-08-01 |
| publisher | Wiley-VCH |
| record_format | Article |
| series | Electrochemical Science Advances |
| spelling | doaj.art-a3e87d3ba77345cba7c02074bd7595472022-12-21T23:30:26ZengWiley-VCHElectrochemical Science Advances2698-59772021-08-0113n/an/a10.1002/elsa.202100002One‐pot multistep electrochemical strategy for the modular synthesis of epoxides, glycols, and aldehydes from alkenesWolfgang Jud0C. Oliver Kappe1David Cantillo2Institute of Chemistry University of Graz NAWI Graz Graz AustriaInstitute of Chemistry University of Graz NAWI Graz Graz AustriaInstitute of Chemistry University of Graz NAWI Graz Graz AustriaAbstract Oxidative functionalization of alkenes is a versatile strategy for the preparation of many oxygen‐containing scaffolds, such as epoxides, diols, or carbonyl‐containing compounds. In addition to conventional chemical methods, which rely on the utilization of stoichiometric amounts of oxidizing reagents, some electrochemical procedures have been developed to achieve these transformations. Typical electrochemical procedures employ tailored and often complex redox mediators to achieve the target transformation. Herein we present a modular approach for the synthesis of epoxides, diols, and aldehydes from a single set of reaction components. With sodium bromide as an inexpensive electrocatalyst and water as the oxygen donor, the outcome of the reaction (epoxide, 1,2‐diol, or aldehyde) can be selected by simply tuning the electrolysis conditions. This convenient platform has been accomplished by developing a selective one‐pot three‐step bromide‐electrocatalyzed epoxidation/ring opening/carbon‐carbon cleavage sequence. Its modularity permits the selection of the desired product, as the sequential reaction can be ended when the target compound has been formed. The method has been applied to a diversely functionalized terminal and non‐terminal olefins.https://doi.org/10.1002/elsa.202100002anodic oxidationdihydroxylationelectroorganic synthesisepoxidationoxidative cleavage |
| spellingShingle | Wolfgang Jud C. Oliver Kappe David Cantillo One‐pot multistep electrochemical strategy for the modular synthesis of epoxides, glycols, and aldehydes from alkenes Electrochemical Science Advances anodic oxidation dihydroxylation electroorganic synthesis epoxidation oxidative cleavage |
| title | One‐pot multistep electrochemical strategy for the modular synthesis of epoxides, glycols, and aldehydes from alkenes |
| title_full | One‐pot multistep electrochemical strategy for the modular synthesis of epoxides, glycols, and aldehydes from alkenes |
| title_fullStr | One‐pot multistep electrochemical strategy for the modular synthesis of epoxides, glycols, and aldehydes from alkenes |
| title_full_unstemmed | One‐pot multistep electrochemical strategy for the modular synthesis of epoxides, glycols, and aldehydes from alkenes |
| title_short | One‐pot multistep electrochemical strategy for the modular synthesis of epoxides, glycols, and aldehydes from alkenes |
| title_sort | one pot multistep electrochemical strategy for the modular synthesis of epoxides glycols and aldehydes from alkenes |
| topic | anodic oxidation dihydroxylation electroorganic synthesis epoxidation oxidative cleavage |
| url | https://doi.org/10.1002/elsa.202100002 |
| work_keys_str_mv | AT wolfgangjud onepotmultistepelectrochemicalstrategyforthemodularsynthesisofepoxidesglycolsandaldehydesfromalkenes AT coliverkappe onepotmultistepelectrochemicalstrategyforthemodularsynthesisofepoxidesglycolsandaldehydesfromalkenes AT davidcantillo onepotmultistepelectrochemicalstrategyforthemodularsynthesisofepoxidesglycolsandaldehydesfromalkenes |