Abstract
In the presence of catalytic amount of Pd(OAc)2, allylic phosphates reacted with trimethylsilyl cyanide (TMSCN) to afford the corresponding allylic isonitriles exclusively. No allylic nitriles, which are selectively obtained in the traditional Pd(0)-catalyzed reaction, were observed. The use of phosphate as the leaving group was crucial to achieve complete regioselectivity of the ambident cyanide species as the N-terminus nucleophile. The reaction was applicable to a series of aromatic-, heteroaromatic-, vinylic-, and aliphatic-substituted allylic phosphates. The mechanistic studies suggested that the allylic isocyanation was catalyzed by the Pd(II) species, and not by Pd(0).
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