En Route to Direct Cross-Coupling between Carbonyl Derivatives and Allyl Alcohols via Hydrazones

Allylic cross-couplings are pivotal in the organic chemistry toolbox; however, traditional methods require the extensive use of noble metals and are limited to activated substrates. To date, allylic cross-couplings that utilize affordable metals and unactivated allylic alcohols remain unexplored. Herein, we report a distinct coupling of ubiquitous and commercially available aldehydes with unactivated allyl alcohols, which also benefits from generating only water and nitrogen gas as innocuous byproducts. This operationally simple and mild methodology enables the direct allylation of carbonyl derivatives, affording alkene products in moderate to high yields across 40 substrates. The reported conditions tolerate both aryl and alkyl aldehydes, as well as ketones with a variety of functional groups. Notably, our strategy facilitates the expedited synthesis of value-added chemicals while producing environmentally benign byproducts.

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Publication Details

Journal
ACS Catalysis
Published
2025-03-27
DOI
https://doi.org/10.1021/acscatal.4c07971
Citations
3
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
2.81

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article

En Route to Direct Cross-Coupling between Carbonyl Derivatives and Allyl Alcohols via Hydrazones

Chao‐Jun Li, Rustam Z. Khaliullin, Ruohua Gui, Faraz Alaghemand
3 citations
ACS Catalysis
Cyclopropane Reaction Mechanisms
2.81
article

En Route to Direct Cross-Coupling between Carbonyl Derivatives and Allyl Alcohols via Hydrazones

Chao‐Jun Li, Rustam Z. Khaliullin, Ruohua Gui, Faraz Alaghemand
article en
3 citations

Abstract

Allylic cross-couplings are pivotal in the organic chemistry toolbox; however, traditional methods require the extensive use of noble metals and are limited to activated substrates. To date, allylic cross-couplings that utilize affordable metals and unactivated allylic alcohols remain unexplored. Herein, we report a distinct coupling of ubiquitous and commercially available aldehydes with unactivated allyl alcohols, which also benefits from generating only water and nitrogen gas as innocuous byproducts. This operationally simple and mild methodology enables the direct allylation of carbonyl derivatives, affording alkene products in moderate to high yields across 40 substrates. The reported conditions tolerate both aryl and alkyl aldehydes, as well as ketones with a variety of functional groups. Notably, our strategy facilitates the expedited synthesis of value-added chemicals while producing environmentally benign byproducts.

ACS CatalysisVol. 15(8)
Green Chemistry (PL), McGill University (CA)
McGill University, Canada Foundation for Innovation, Canada Research Chairs, Fonds Québécois de la Recherche sur la Nature et les Technologies, Natural Sciences and Engineering Research Council of Canada
Openalex Percentile: Top 11%
Cyclopropane Reaction Mechanisms
2.81
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En Route to Direct Cross-Coupling between Carbonyl Derivatives and Allyl Alcohols via Hydrazones — Chao‐Jun Li, Rustam Z. Khaliullin, et al. · ACS Catalysis (2025) | TGRS Research Map | TGRS