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Please login to access the full content or check if you have access via Method 3: Reaction of Organozinc Compounds Bearing Cyano Groups with Electrophiles

DOI: 10.1055/sos-SD-019-00220

Murahashi, S.-I.Science of Synthesis, (200419360.

Organozinc halides are readily prepared by the insertion of zinc dust into organic halides[‌96‌] or by low-temperature transmetalation of organolithium with zinc salts.[‌97‌,‌98‌] They display an excellent functional-group tolerance allowing the convenient preparation of polyfunctional organozinc compounds. Their moderate reactivity toward carbon electrophiles necessitates transmetalation to the more reactive organocopper or use of a transition-metal (e.g., palladium-based) catalyst.[‌99‌,‌100‌] However, the commercially available tosyl cyanide[‌101‌] reacts readily with various organozinc compounds affording polyfunctional nitriles in good yields.[‌102‌]

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