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 language | English |
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Pages (from-to) | 1910-1915 |
Number of pages | 6 |
Journal | Advanced Synthesis and Catalysis |
Volume | 358 |
Issue number | 12 |
DOIs | |
Publication status | Published - 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.
Funders | Funder number |
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National Institutes of Health | |
National Institute of General Medical Sciences | 104349 |
Consejo Nacional de Ciencia y Tecnología | |
Türkiye Bilimsel ve Teknolojik Araştirma Kurumu |
Keywords
- 2-azaallyl anion
- diarylmethylamines
- NIXANTPHOS
- regioselectivity
- umpolung