Functionalization of Alkenyl C–H Bonds with D2O via Pd(0)/Carboxylic Acid Catalysis

Nicola Camedda; Andrea Serafino; Raimondo Maggi; Franca Bigi; Gianpiero Cera; Giovanni Maestri

doi:10.1055/s-0039-1690892

Synthesis, Table of Contents

Synthesis 2020; 52(12): 1762-1772
DOI: 10.1055/s-0039-1690892

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Functionalization of Alkenyl C–H Bonds with D₂O via Pd(0)/Carboxylic Acid Catalysis

Nicola Camedda

^aUniversità di Parma, Dipartimento di Scienze Chimiche, della Vita e della Sostenibilità Ambientale, Parco Area delle Scienze 17/A, 43124 Parma, Italy

,

Andrea Serafino

^aUniversità di Parma, Dipartimento di Scienze Chimiche, della Vita e della Sostenibilità Ambientale, Parco Area delle Scienze 17/A, 43124 Parma, Italy

,

Raimondo Maggi

^aUniversità di Parma, Dipartimento di Scienze Chimiche, della Vita e della Sostenibilità Ambientale, Parco Area delle Scienze 17/A, 43124 Parma, Italy

,

Franca Bigi

^aUniversità di Parma, Dipartimento di Scienze Chimiche, della Vita e della Sostenibilità Ambientale, Parco Area delle Scienze 17/A, 43124 Parma, Italy

^bIMEM-CNR, Parco Area delle Scienze 37/A, 43124 Parma, Italy Email: giovanni.maestri@unipr.it

,

Gianpiero Cera

^aUniversità di Parma, Dipartimento di Scienze Chimiche, della Vita e della Sostenibilità Ambientale, Parco Area delle Scienze 17/A, 43124 Parma, Italy

,

Giovanni Maestri∗

^aUniversità di Parma, Dipartimento di Scienze Chimiche, della Vita e della Sostenibilità Ambientale, Parco Area delle Scienze 17/A, 43124 Parma, Italy

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Abstract

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Abstract

We report herein a simple catalytic method for the extensive labeling of alkenyl C–H bonds through the combination of a palladium(0) complex and a carboxylic acid in the presence of deuterium oxide. The reaction can be applied to a variety of terminal alkenes and the best results are obtained with aryl-substituted examples. This method represents a convenient approach for the preparation of extensively labeled chemicals from the cheapest and safest source of deuterium.

Key words

palladium - hydrides - deuterium - C–H functionalization - alkenes - catalysis

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References

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Supplementary Material

Supporting Information