Highly stereoselective synthesis of <i>trans</i>-alkenes <i>via</i> electrochemical Ni-catalyzed hydroarylation of alkynes with aryl iodides

Zhang, Haoxiang; Guo, Lin; Yang, Chao; Xia, Wujiong

doi:10.1039/d3ob00705g

Org. Biomol. Chem.

2023

DOI: 10.1039/d3ob00705g

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Highly stereoselective synthesis of trans-alkenes via electrochemical Ni-catalyzed hydroarylation of alkynes with aryl iodides

Haoxiang Zhang

Lin Guo

Chao Yang

et al.

Abstract: An electrochemical nickel catalyzed hydroarylation reaction of various alkynes is herein described. In this reaction, alkynes were coupled with Aryl Iodides by electrochemical Ni-catalysis to obtain highly selective trans-olefins.The outstanding...

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2024

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Synthesis of Stilbenes by Cyanide/Base-Mediated Coupling of Benzylic Chlorides and Alcohols

Madsen,

Schichler

2024

Synthesis

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A straightforward procedure has been developed for the direct synthesis of stilbenes from benzylic chlorides and alcohols. The transformation employs a two-step one-pot protocol where the benzylic chloride is first subjected to a substitution with potassium cyanide in o-xylene. Without workup, the resulting arylacetonitrile is then reacted directly with the benzylic alcohol and potassium tert-butoxide to generate the stilbene framework. The condensation has been performed with a variety of commercially available benzylic chlorides and alcohols to afford substituted stilbenes as the pure (E) isomers. A kinetic isotope effect of 5.2 has been measured for the overall transformation when comparing benzyl alcohol and α,α-d2-benzyl alcohol. The release of cyanide during the final elimination to stilbene has been confirmed by a picrate test. Thus, the potassium tert-butoxide-mediated elimination of cyanide is believed to proceed by an E1cB mechanism where the deprotonation reaction constitutes the rate-determining step.

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Synthesis of Stilbenes by Cyanide/Base-Mediated Coupling of Benzylic Chlorides and Alcohols

Madsen,

Schichler

2024

Synthesis

View full text Add to dashboard Cite

show abstract

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Highly stereoselective synthesis of trans-alkenes via electrochemical Ni-catalyzed hydroarylation of alkynes with aryl iodides

Abstract: An electrochemical nickel catalyzed hydroarylation reaction of various alkynes is herein described. In this reaction, alkynes were coupled with Aryl Iodides by electrochemical Ni-catalysis to obtain highly selective trans-olefins.The outstanding...

Cited by 1 publication

References 58 publications

Synthesis of Stilbenes by Cyanide/Base-Mediated Coupling of Benzylic Chlorides and Alcohols

Synthesis of Stilbenes by Cyanide/Base-Mediated Coupling of Benzylic Chlorides and Alcohols

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