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Nitrile Alkylations through Sulfinyl–Metal Exchange


  • Financial support from the National Science Foundation (USA) is gratefully acknowledged (CHE 1111406, 0808996, 0421252 HRMS, and 0614785 for NMR facilities).


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Triple alkylation: Phenylsulfinyl- and phenylthioacetonitrile can function as trianion equivalents of acetonitrile by sequential alkylation and sulfinyl–metal exchange (see scheme; mCPBA=meta-chloroperoxybenzoic acid). The metalated nitriles alkylate a range of electrophiles to obtain nitriles with quaternary centers. The sulfinyl–metal exchange proceeds under very mild conditions and has a high functional-group tolerance.

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