Highly efficient palladium-catalyzed cross-coupling of diarylborinic acids with arenediazoniums for practical diaryl synthesis

[Display omitted] •Cost-effective arylboron reagent.•Good functional group compatibility.•Low loading of simple ligandless catalyst.•Mild, open-flask and base-free conditions.•High efficacy to heteroatom ortho-substituted diazoniums. A highly efficient cross-coupling of cost-effective diarylborinic...

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Veröffentlicht in:Tetrahedron letters 2020-02, Vol.61 (7), p.151491, Article 151491
Hauptverfasser: Wang, Fengze, Wang, Chen, Sun, Guoping, Zou, Gang
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Sprache:eng
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Zusammenfassung:[Display omitted] •Cost-effective arylboron reagent.•Good functional group compatibility.•Low loading of simple ligandless catalyst.•Mild, open-flask and base-free conditions.•High efficacy to heteroatom ortho-substituted diazoniums. A highly efficient cross-coupling of cost-effective diarylborinic acids with both isolatable and latent arenediazoniums, i.e. tetrafluoroborates and aryltriazenes, respectively, has been developed with a practical palladium catalyst system under base-free conditions in open flask at room temperature. A variety of electronically and sterically various biaryls, in particular, those bearing a coordinative ortho-substituent, could be obtained in good to excellent yields by using 0.3 mol% palladium acetate as catalyst. Features of the protocol including cost-effectiveness of diarylborinic acids, efficacy to heteroatom ortho-substituted substrates and high chemoselectivity to aryl chlorides have been clearly demonstrated in practical synthesis of fungicide Boscalid.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2019.151491