Ligandcontrolled Regiodivergent C-H Alkenylation of Pyrazoles and its Application to the Synthesis of Indazoles
- Ligandcontrolled Regiodivergent C-H Alkenylation of Pyrazoles and its Application to the Synthesis of Indazoles
- 임상민; 김현태; 하혜리; 강근희; 김옥순; 류호; Abul Kalam Biswas; 백무현; 주정민
- alkenylation; C-H activation; indazole; palladium; pyrazole
- Issue Date
- Angewandte Chemie international edition
- VOL 56, NO 51-16266
- Regioselective C4-, C5-, and di-alkenylations of pyrazoles were achieved. An electrophilic Pd catalyst generated by trifluoroacetic acid (TFA) and 4,5-diazafluoren-9-one (DAF) leads to C4-alkenylation, whereas KOAc and mono-protected amino acid (MPAA) ligand Ac-Val-OH give C5-alkenylation. A combination of palladium acetate, silver carbonate, and pivalic acid affords dialkenylation products. Annulation through sequential alkenylation, thermal 6 pi-electrocyclization, and oxidation gives functionalized indazoles. This comprehensive strategy greatly expands the range of readily accessible pyrazole and indazole derivatives, enabling useful regiodivergent C-H functionalization of pyrazoles and other heteroaromatic systems.
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