Electroreduction Enables Regioselective 1,2‐Diarylation of Alkenes with Two Electrophiles

AbstractPrecisely introducing two similar functional groups into bulk chemical alkenes represents a formidable route to complex molecules. Especially, the selective activation of two electrophiles is in crucial demand, yet challenging for cross‐electrophile‐coupling. Herein, we demonstrate a redox‐mediated electrolysis, in which aryl nitriles are both aryl radical precursors and redox‐mediators, enables an intermolecular alkene 1,2‐diarylation with a remarkable regioselectivity, thereby avoiding the involvement of transition‐metal catalysts. This transformation utilizes cyanoarene radical anions for activating various aryl halides (including iodides, bromides, and even chlorides) and affords 1,2‐diarylation adducts in up to 83 % yield and >20 : 1 regioselectivity with more than 80 examples, providing a feasible approach to complex bibenzyl derivatives.

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Metrics

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Citations

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References

Details

Published: Mar 14, 2023
Vol/Issue: 62(17)
License: View

Authors

W

Weijie Yu

National Research Center for Carbohydrate Synthesis Key Lab of Fluorine and Silicon for Energy Materials and Chemistry of Ministry of Education and Jiangxi Province Key Laboratory of Chemical Biology Jiangxi Normal University Nanchang 330022, Jiangxi P. R. China

S

Shengchun Wang

The Institute for Advanced Studies (IAS) and College of Chemistry and Molecular Sciences Wuhan University Wuhan 430072, Hubei P. R. China

M

Meng He

The Institute for Advanced Studies (IAS) and College of Chemistry and Molecular Sciences Wuhan University Wuhan 430072, Hubei P. R. China

Z

Zhou Jiang

National Research Center for Carbohydrate Synthesis Key Lab of Fluorine and Silicon for Energy Materials and Chemistry of Ministry of Education and Jiangxi Province Key Laboratory of Chemical Biology Jiangxi Normal University Nanchang 330022, Jiangxi P. R. China

Y

Yi Yu

The Institute for Advanced Studies (IAS) and College of Chemistry and Molecular Sciences Wuhan University Wuhan 430072, Hubei P. R. China

J

Jinping Lan

National Research Center for Carbohydrate Synthesis Key Lab of Fluorine and Silicon for Energy Materials and Chemistry of Ministry of Education and Jiangxi Province Key Laboratory of Chemical Biology Jiangxi Normal University Nanchang 330022, Jiangxi P. R. China

J

Jin Luo

National Research Center for Carbohydrate Synthesis Key Lab of Fluorine and Silicon for Energy Materials and Chemistry of Ministry of Education and Jiangxi Province Key Laboratory of Chemical Biology Jiangxi Normal University Nanchang 330022, Jiangxi P. R. China

P

Pengjie Wang

The Institute for Advanced Studies (IAS) and College of Chemistry and Molecular Sciences Wuhan University Wuhan 430072, Hubei P. R. China

X

Xiaotian Qi

The Institute for Advanced Studies (IAS) and College of Chemistry and Molecular Sciences Wuhan University Wuhan 430072, Hubei P. R. China

T

Tao Wang

National Research Center for Carbohydrate Synthesis Key Lab of Fluorine and Silicon for Energy Materials and Chemistry of Ministry of Education and Jiangxi Province Key Laboratory of Chemical Biology Jiangxi Normal University Nanchang 330022, Jiangxi P. R. China

A

Aiwen Lei

National Research Center for Carbohydrate Synthesis Key Lab of Fluorine and Silicon for Energy Materials and Chemistry of Ministry of Education and Jiangxi Province Key Laboratory of Chemical Biology Jiangxi Normal University Nanchang 330022, Jiangxi P. R. China; The Institute for Advanced Studies (IAS) and College of Chemistry and Molecular Sciences Wuhan University Wuhan 430072, Hubei P. R. China

Funding

National Natural Science Foundation of China Award: 22031008

National Key Research and Development Program of China Award: 2021YFA1500100

Cite This Article

Weijie Yu, Shengchun Wang, Meng He, et al. (2023). Electroreduction Enables Regioselective 1,2‐Diarylation of Alkenes with Two Electrophiles. Angewandte Chemie International Edition, 62(17). https://doi.org/10.1002/anie.202219166

Electroreduction Enables Regioselective 1,2‐Diarylation of Alkenes with Two Electrophiles

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