Palladium-catalyzed cross-coupling reactions of triarylbismuthanes with terminal alkynes under aerobic conditions

• A Sonogashira-type reaction by using triarylbismuthanes was developed.
• All three aryl groups on bismuth could be transferred to the coupling product.
• A wide range of Ar3Bi furnished internal alkynes in good to excellent yield.

A simple Pd-catalyzed Sonogashira-type cross-coupling reaction using of triarylbismuthanes is described. The reaction of triarylbismuthanes with terminal alkynes in the presence of 5 mol% of Pd(OAc)2, 6 equiv. AgF and 6 equiv. K3PO4 at room temperature afforded the coupling products in good to excellent yield. The reaction proceeded effectively under aerobic conditions, and all three aryl groups on bismuth could be transferred to the coupling products. The reaction was sensitive to the electronic nature of the triarylbismuthanes: substrates bearing an electron-withdrawing group on the aromatic ring showed higher reactivity than those having an electron-donating group.

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