Use of tunable ligands allows for intermolecular Pd-catalyzed C--O bond formation |
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Authors: | Vorogushin Andrei V Huang Xiaohua Buchwald Stephen L |
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Institution: | Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA. |
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Abstract: | Bulky biaryl phosphine ligands facilitate Pd-catalyzed C-O coupling reactions of aryl halides with primary and secondary alcohols by promoting reductive elimination at the expense of beta-hydride elimination. The key to their success is the ability to match the size of the ligand to that of the combination of substrates. The efficient coupling of a number of unactivated aryl chlorides and bromides with cyclic and acyclic secondary alcohols was achieved. This included the coupling of allylic alcohols for the first time in a Pd-catalyzed coupling process. |
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