Literature DB >> 28190996

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

Minyan Li1, Baris Yucel1,2, Jacqueline Jiménez1,3, Madeline Rotella1, Yue Fu1, Patrick J Walsh1.   

Abstract

An umpolung synthesis of diarylmethylamine derivatives is presented. This reaction entails a Pd 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 glovebox.

Entities:  

Keywords:  2-azaallyl anion; NIXANTPHOS; diarylmethylamines; regioselectivity; umpolung

Year:  2016        PMID： 28190996      PMCID： PMC5298571          DOI： 10.1002/adsc.201600075

Source DB:  PubMed          Journal:  Adv Synth Catal        ISSN： 1615-4150            Impact factor:   5.837


  24 in total

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Authors:  S Lee; N A Beare; J F Hartwig
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2.  Synthesis of diarylmethylamines via palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions.

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Journal:  J Am Chem Soc       Date:  2006-08-09       Impact factor: 15.419

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3.  Arylation of Azaarylmethylamines with Aryl Chlorides and a NiBr2/NIXANTPHOS-based Catalyst.

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5.  Direct Catalytic Asymmetric Synthesis of Trifluoromethylated γ-Amino Esters/Lactones via Umpolung Strategy.

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6.  Transition-Metal-Free Radical C(sp3)-C(sp2) and C(sp3)-C(sp3) Coupling Enabled by 2-Azaallyls as Super-Electron-Donors and Coupling-Partners.

Authors:  Minyan Li; Simon Berritt; Lucas Matuszewski; Guogang Deng; Ana Pascual-Escudero; Grace B Panetti; Michal Poznik; Xiaodong Yang; Jason J Chruma; Patrick J Walsh
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8.  SET activation of nitroarenes by 2-azaallyl anions as a straightforward access to 2,5-dihydro-1,2,4-oxadiazoles.

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10.  Transition-metal-free allylation of 2-azaallyls with allyl ethers through polar and radical mechanisms.

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  10 in total

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