Umpolung Synthesis of Diarylmethylamines via Palladium- Catalyzed Arylation of N-Benzyl Aldimines

Minyan Li, Baris Yucel, Jacqueline Jiménez, Madeline Rotella, Yue Fu, Patrick J. Walsh*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

33 Citations (Scopus)

Abstract

An umpolung synthesis of diarylmethylamine derivatives is presented. This reaction entails a palladium-catalyzed arylation of 1,3-diaryl-2-azaallyl anions, in situ generated from N-benzyl aldimines. A Pd(NIXANTPHOS)-based catalyst together with hindered silylamide bases enabled the coupling of aldimines with aryl bromides in good to excellent yields without product isomerization. Moreover, regioselectivity in the arylation of unsymmetrical 1,3-diaryl-2-azaallyl anions was studied. This method is suitable for a gram scale synthesis of diarylmethylamine derivatives at room temperature without use of a glove box. (Figure presented.) .

Original languageEnglish
Pages (from-to)1910-1915
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume358
Issue number12
DOIs
Publication statusPublished - 16 Jun 2016

Bibliographical note

Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Funding

P.J.W. acknowledges the NIH (National Institute of General Medical Sciences NIGMS 104349). B.Y thanks the Scientific and Technical Research Council of Turkey for a TUBITAK-2219 fellowship. J. J. thanks CONACyT (México) for fellowships.

FundersFunder number
National Institutes of Health
National Institute of General Medical Sciences104349
Consejo Nacional de Ciencia y Tecnología
Türkiye Bilimsel ve Teknolojik Araştirma Kurumu

    Keywords

    • 2-azaallyl anion
    • diarylmethylamines
    • NIXANTPHOS
    • regioselectivity
    • umpolung

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