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Rhodium-catalyzed redox-neutral coupling of phenidones with alkynes.
Org Biomol Chem. 2017 Jul 21; 15(27):5701-5708.OB

Abstract

A switchable synthesis of N-substituted indole derivatives from phenidones via rhodium-catalyzed redox-neutral C-H activation has been achieved. In this protocol, we firstly disclosed that the reactivity of Rh(iii) catalysis could be enhanced through employing palladium acetate as an additive. Some representative features include external oxidant-free, applicable to terminal alkynes, short reaction time and operational simplicity. The utility of this method is further showcased by the economical synthesis of potent anticancer PARP-1 inhibitors.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Fan Z
CAS Key Laboratory of Receptor Research, and the State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica (SIMM), Chinese Academy of Sciences, Shanghai 201203, China. aozhang@simm.ac.cn and University of Chinese Academy of Sciences, Beijing 100049, China.
Lu H
ShanghaiTech University, Shanghai 201210, China.
Li W
CAS Key Laboratory of Receptor Research, and the State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica (SIMM), Chinese Academy of Sciences, Shanghai 201203, China. aozhang@simm.ac.cn.
Geng K
CAS Key Laboratory of Receptor Research, and the State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica (SIMM), Chinese Academy of Sciences, Shanghai 201203, China. aozhang@simm.ac.cn and University of Chinese Academy of Sciences, Beijing 100049, China.
Zhang A
CAS Key Laboratory of Receptor Research, and the State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica (SIMM), Chinese Academy of Sciences, Shanghai 201203, China. aozhang@simm.ac.cn and University of Chinese Academy of Sciences, Beijing 100049, China and ShanghaiTech University, Shanghai 201210, China.

MeSH

AlkynesCatalysisMolecular StructureOrganometallic CompoundsOxidation-ReductionPyrazolesRhodium

Pub Type(s)

Journal Article

Language

eng

PubMed ID

28649682

Citation

Fan, Zhoulong, et al. "Rhodium-catalyzed Redox-neutral Coupling of Phenidones With Alkynes." Organic & Biomolecular Chemistry, vol. 15, no. 27, 2017, pp. 5701-5708.
Fan Z, Lu H, Li W, et al. Rhodium-catalyzed redox-neutral coupling of phenidones with alkynes. Org Biomol Chem. 2017;15(27):5701-5708.
Fan, Z., Lu, H., Li, W., Geng, K., & Zhang, A. (2017). Rhodium-catalyzed redox-neutral coupling of phenidones with alkynes. Organic & Biomolecular Chemistry, 15(27), 5701-5708. https://doi.org/10.1039/c7ob01271c
Fan Z, et al. Rhodium-catalyzed Redox-neutral Coupling of Phenidones With Alkynes. Org Biomol Chem. 2017 Jul 21;15(27):5701-5708. PubMed PMID: 28649682.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhodium-catalyzed redox-neutral coupling of phenidones with alkynes. AU - Fan,Zhoulong, AU - Lu,Heng, AU - Li,Wei, AU - Geng,Kaijun, AU - Zhang,Ao, Y1 - 2017/06/26/ PY - 2017/6/27/pubmed PY - 2018/3/27/medline PY - 2017/6/27/entrez SP - 5701 EP - 5708 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 15 IS - 27 N2 - A switchable synthesis of N-substituted indole derivatives from phenidones via rhodium-catalyzed redox-neutral C-H activation has been achieved. In this protocol, we firstly disclosed that the reactivity of Rh(iii) catalysis could be enhanced through employing palladium acetate as an additive. Some representative features include external oxidant-free, applicable to terminal alkynes, short reaction time and operational simplicity. The utility of this method is further showcased by the economical synthesis of potent anticancer PARP-1 inhibitors. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/28649682/Rhodium_catalyzed_redox_neutral_coupling_of_phenidones_with_alkynes_ L2 - https://doi.org/10.1039/c7ob01271c DB - PRIME DP - Unbound Medicine ER -