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Nickel-Catalyzed Selective C–H Cyanation via Aromatic Thianthrenium Salts

Guofu Zhang, Zijin Luo, Chenfei Guan, Xianghao Zhang, Chengrong Ding

2023The Journal of Organic Chemistry21 citationsDOI

Abstract

Here, we report the first case of nickel-catalyzed C–H cyanation via arylthianthrenium salts. The reaction features the use of air-stable and inexpensive NiCl 2 ·6H 2 O as a catalyst for the highly selective construction of cyanation products by aromatic pre-thianthrenation. The mechanism study shows that the formation of aryl radicals is involved. Also, this protocol can be applied to the late-stage functionalization of bioactive molecules and is readily scalable, further showcasing the synthetic utility.

Topics & Concepts

CyanationCatalysisNickelChemistryMedicinal chemistryOrganic chemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsSulfur-Based Synthesis Techniques
Nickel-Catalyzed Selective C–H Cyanation via Aromatic Thianthrenium Salts | Litcius