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| - Pd-Catalyzed Amidations of Aryl Chlorides UsingMonodentate Biaryl Phosphine Ligands: A Kinetic,Computational, and Synthetic Investigation
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| - We present results on the amidation of aryl halides and sulfonates utilizing a monodentate biarylphosphine-Pd catalyst. Our results are in accord with a previous report that suggests that the formation ofκ2-amidate complexes is deleterious to the effectiveness of a catalyst for this transformation and that theirformation can be prevented by the use of appropriate bidentate ligands. We now provide data that suggestthat the use of certain monodentate ligands can also prevent the formation of the κ2-amidate complexesand thereby generate more stable catalysts for the amination of aryl chlorides. Furthermore, computationalstudies shed light on the importance of the key feature(s) of the biaryl phosphines (a methyl group orthoto the phosphorus center) that enable the coupling to occur. The use of ligands that possess a methylgroup ortho to the phosphorus center allows a variety of aryl and heteroaryl chlorides with various amidesto be coupled in high yield.
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