Journal article

Publication year: 2019

Pages: 493-498

Journal: Accounts and Rapid Communications in Chemical Synthesis

Volume number: 30

Issue number: 4

ISSN: 0936-5214

Open access status: Hybrid

DOI Link: https://doi.org/10.1055/s-0037-1610403

Publisher: Thieme

Abstract: 
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.

Harvard Citation style: Berndt, J., Erb, F., Ochmann, L., Beppler, J. and Schreiner, P. (2019) Selective Phthalimido-N-oxyl (PINO)-Catalyzed C-H Cyanation of Adamantane Derivatives, Accounts and Rapid Communications in Chemical Synthesis, 30(4), pp. 493-498. https://doi.org/10.1055/s-0037-1610403

APA Citation style: Berndt, J., Erb, F., Ochmann, L., Beppler, J., & Schreiner, P. (2019). Selective Phthalimido-N-oxyl (PINO)-Catalyzed C-H Cyanation of Adamantane Derivatives. Accounts and Rapid Communications in Chemical Synthesis. 30(4), 493-498. https://doi.org/10.1055/s-0037-1610403