CuBr/H2O2-Mediated Oxidative Coupling ofN,N-Dialkylarylamines in ­Water: A Practical Synthesis of Benzidine Derivatives

In this study, a heterogeneous rhodium-catalyzed oxidative homocoupling reaction of anilines utilizing molecular oxygen as the sole oxidant is reported. Employing a commercially available and recyclable Rh/C catalyst enabled the oxidative dimerization of various anilines, including N,N-disubstituted and N-monosubstituted anilines, as well as diarylamines, triarylamines, and carbazoles. Additionally, the catalytic protocol was extended to the ortho−ortho coupling of anilines, affording 2,2′-diaminobiphenyls with high regioselectivity. Notably, the developed approach provides rapid access to diversely functionalized benzidines and diaminobiphenyls in an operationally simple, practical, and environmentally friendly manner.

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Catalytic and Aerobic Oxidative Biaryl Coupling of Anilines Using a Recyclable Heterogeneous Catalyst for Synthesis of Benzidines and Bicarbazoles

Matsumoto

Toubaru

Tachikawa

et al. 2020

J. Org. Chem.

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CuBr/H₂O₂-Mediated Oxidative Coupling ofN,N-Dialkylarylamines in Water: A Practical Synthesis of Benzidine Derivatives

Abstract: CuBr/H 2 O 2 was deployed into mediating the oxidative coupling reaction of N,N-dialkylarylamines in water, which gave benzidine derivatives in an economically and environmentally satisfying manner.

Cited by 1 publication

References 24 publications

Catalytic and Aerobic Oxidative Biaryl Coupling of Anilines Using a Recyclable Heterogeneous Catalyst for Synthesis of Benzidines and Bicarbazoles

Catalytic and Aerobic Oxidative Biaryl Coupling of Anilines Using a Recyclable Heterogeneous Catalyst for Synthesis of Benzidines and Bicarbazoles

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CuBr/H2O2-Mediated Oxidative Coupling ofN,N-Dialkylarylamines in ­Water: A Practical Synthesis of Benzidine Derivatives

Abstract: CuBr/H 2 O 2 was deployed into mediating the oxidative coupling reaction of N,N-dialkylarylamines in water, which gave benzidine derivatives in an economically and environmentally satisfying manner.

Cited by 1 publication

References 24 publications

Catalytic and Aerobic Oxidative Biaryl Coupling of Anilines Using a Recyclable Heterogeneous Catalyst for Synthesis of Benzidines and Bicarbazoles

Catalytic and Aerobic Oxidative Biaryl Coupling of Anilines Using a Recyclable Heterogeneous Catalyst for Synthesis of Benzidines and Bicarbazoles

Contact Info

Product

Resources

About

CuBr/H₂O₂-Mediated Oxidative Coupling ofN,N-Dialkylarylamines in Water: A Practical Synthesis of Benzidine Derivatives