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 |
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Sprache: | eng |
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•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. |
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ISSN: | 0040-4039 1873-3581 |
DOI: | 10.1016/j.tetlet.2019.151491 |