The cyanation of 3-bromopyridine catalyzed by in situ generated Ni(PPh3)n was examined with various MCN (M = K, Na)-dipolar aprotic solvent systems by four procedures. Under certain reaction conditions, 3-bromopyridine and several heteroaromatic halides were cyanated to give the corresponding nitriles in fair to good yields. Noticeable differences in reactivity among 3-bromopyridine, 3-bromofuran, 3-bromothiophene, and bromobenzene were observed.
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