Synlett

Versatile and Fluoride-Free Cyanation of Alkyl Halides and Sulfonates with Trimethylsilyl Cyanide

O Yabe, H Mizufune, T Ikemoto

Index: Yabe, Osamu; Mizufune, Hideya; Ikemoto, Tomomi Synlett, 2009 , # 8 p. 1291 - 1294

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Abstract

Abstract Cyanation of biphenyl-4-ylmethyl methanesulfonate with trimethylsilyl cyanide using fluoride-free inorganic salts, such as Cs 2 CO 3, K 2 CO 3, and LiOHH 2 O, as additives in MeCN quantitatively gave biphenyl-4-ylacetonitrile. This methodology was applied to various alkyl halides to give the corresponding nitrile compounds in good to excellent yields. Of note, 4-(hydroxymethyl) benzyliodide O-protected by the silyl group ...

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