Cobalt-Catalyzed Photoelectrochemical Dehydration of Primary Alcohols

The direct and selective dehydration of primary alcohols remains a longstanding challenge due to the instability of primary carbocations and the high barrier associated with alkene-like E2 transition states. Here we report a cobalt-catalyzed, photoelectrochemical strategy for the direct conversion of primary alcohols to terminal alkenes. The reaction proceeds in an undivided cell under blue-light irradiation, employing a readily available CoCl<sub>2</sub>/dimethylglyoxime (dmgH<sub>2</sub>) catalyst system. This method displays broad substrate scope, high regioselectivity across polyol frameworks, and exceptional tolerance of oxidation-sensitive functional groups, enabling late-stage diversification of natural products and drug derivatives. Mechanistic studies support a radical-based catalytic cycle initiated by anodic alcohol activation and completed via light-driven β-hydrogen abstraction. In contrast, without irradiation, the same conditions yield deoxygenated alkanes via a mechanistically distinct, electroreductive Co-C bond homolysis and HAT pathway. Together, these findings establish a mild and general platform for direct and selective dehydration of primary alcohols.

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Publication Details

Journal
Journal of the American Chemical Society
Published
2025-11-21
DOI
https://doi.org/10.1021/jacs.5c15270
Citations
2
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
1.87
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article

Cobalt-Catalyzed Photoelectrochemical Dehydration of Primary Alcohols

Xiaoyuan Ying, Chao Li, Yong Zhang
2 citations
Journal of the American Chemical Society
Radical Photochemical Reactions
1.87
article

Cobalt-Catalyzed Photoelectrochemical Dehydration of Primary Alcohols

Xiaoyuan Ying, Chao Li, Yong Zhang
article en
2 citations

Abstract

The direct and selective dehydration of primary alcohols remains a longstanding challenge due to the instability of primary carbocations and the high barrier associated with alkene-like E2 transition states. Here we report a cobalt-catalyzed, photoelectrochemical strategy for the direct conversion of primary alcohols to terminal alkenes. The reaction proceeds in an undivided cell under blue-light irradiation, employing a readily available CoCl<sub>2</sub>/dimethylglyoxime (dmgH<sub>2</sub>) catalyst system. This method displays broad substrate scope, high regioselectivity across polyol frameworks, and exceptional tolerance of oxidation-sensitive functional groups, enabling late-stage diversification of natural products and drug derivatives. Mechanistic studies support a radical-based catalytic cycle initiated by anodic alcohol activation and completed via light-driven β-hydrogen abstraction. In contrast, without irradiation, the same conditions yield deoxygenated alkanes via a mechanistically distinct, electroreductive Co-C bond homolysis and HAT pathway. Together, these findings establish a mild and general platform for direct and selective dehydration of primary alcohols.

Journal of the American Chemical SocietyVol. 147(49)
Peking University (CN), National Institute of Biological Sciences, Beijing (CN), Center for Interdisciplinary Studies (IN), Tsinghua University (CN)
Openalex Percentile: Top 13%
Radical Photochemical Reactions
1.87
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