101901-51-3Relevant articles and documents
Selective Phthalimido-N-oxyl (PINO)-Catalyzed C-H Cyanation of Adamantane Derivatives
Berndt, Jan-Philipp,Erb, Frederik R.,Ochmann, Lukas,Beppler, Jaqueline,Schreiner, Peter R.
, p. 493 - 498 (2019)
We present a new method for the selective C(sp 3)-H cyanation of adamantane derivatives with PINO as the hydrogen abstracting reagent. A cyano radical is thereby transferred from p - toluenesulfonyl cyanide, allowing the cyanation of adamantane derivatives in up to 71% yield. The protocol presents a novel way to orthogonally functionalized adamantanes that are otherwise difficult to prepare. Mechanistic studies support the hypothesis of a radical pathway.