Late-Stage Diversification of Biarylphosphines through Rhodium(I)-Catalyzed C–H Bond Alkenylation with Internal Alkynes
journal contributionposted on 09.07.2020, 16:05 by Zhuan Zhang, Marie Cordier, Pierre H. Dixneuf, Jean-François Soulé
We report herein P(III)-directed C–H bond alkenylation of (dialkyl)- and (diaryl)biarylphosphines using internal alkynes. Chloride-free [Rh(OAc)(COD)]2 acts as a better catalyst than commercially available [RhCl(COD)]2. Conditions were developed to control the mono- and difunctionalization depending on the alkyne stoichiometry. One of these novel bisalkenylated (dialkyl)biarylphosphines was employed for the preparation of a palladium(II) complex, and some of these functionalized ligands outperformed their corresponding unfunctionalized phosphines in Pd-catalyzed amidation with sterically hindered aryl chlorides.
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Internal AlkynesstericallyPd-catalyzed amidationalkyne stoichiometryRhodiumRhdifunctionalizationnovel bisalkenylatedAlkenylationdialkylunfunctionalized phosphinesfunctionalized ligandsaryl chloridescatalystLate-Stage DiversificationdiarylpalladiumBondRhClBiarylphosphinepreparationChloride-freealkenylationbond