Regiodivergent Cu-Promoted, AcOH-Switchable Distal Versus Proximal Direct Cyanation of 1-Aryl-1H-indazoles and 2-Aryl-2H-indazoles via Aerobic Oxidative C–H Bond ActivationClick to copy article linkArticle link copied!
- Richa SharmaRicha SharmaLaboratory of Organic and Medicinal Chemistry, Department of Chemistry, Malaviya National Institute of Technology, Jawaharlal Nehru Marg, Jaipur 302017, IndiaMore by Richa Sharma
- Sandeep Chaudhary*Sandeep Chaudhary*Email: [email protected], [email protected]. Phone: 91-141-2713319, 91-522-2497903. Fax: 91-141-2529029, 91-522-2975587.Laboratory of Organic and Medicinal Chemistry, Department of Chemistry, Malaviya National Institute of Technology, Jawaharlal Nehru Marg, Jaipur 302017, IndiaLaboratory of Bioactive Heterocycles and Catalysis, Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research-Raebareli (Transit Campus), Bijnor−Sisendi Road, Near CRPF Base Camp, Sarojini Nagar, Lucknow 226002, IndiaMore by Sandeep Chaudhary
Abstract
A copper-promoted regiodivergent, AcOH-switchable, distal and proximal direct cyanation of N-aryl-(1H/2H)-indazoles via aerobic oxidative C(sp2)–H bond activation has been developed. The inclusion or exclusion of AcOH as an additive is the foremost cause for the positional switch in the C–CN bond formation method that results in (C-2′)-cyanated 2-aryl-2H-indazoles 3a–j, (C-2′)-cyanated 1-aryl-1H-indazoles 4a–j [distal], or C-3 cyanated 2-aryl-2H-indazoles 5a–i [proximal] products in good to excellent yields and showed various functional group tolerance. The cyanide (CN–) ion surrogate was generated via the unification of dimethylformamide and ammonium iodide (NH4I). The utilization of molecular oxygen (aerobic oxidative strategy) as a clean and safe oxidant is liable for generous value addition. The further pertinence of the developed protocol has been demonstrated by transforming the synthesized cyanated product into numerous other functional groups, which will, undoubtedly, accomplish utilization in the synthetic area of biologically important compounds and medicinal chemistry.
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