The cyanation of aryl halides with powdered NaCN in dioxane is efficiently catalyzed by crowned phosphine complexes of palladium to give aryl cyanides in good yields. Owing to the proximity effect of the crowned complexes, the catalytic efficiency is superior to those of mixed systems of unmodified phospine complexes of palladium with the corresponding crown ethers.
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Okano et al. (1998) studied this question.