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Palladium-Catalyzed [2 + 2 + 1] Annulation of Alkyne-Tethered Aryl Iodides with Diaziridinone: Synthesis of 3,4-Fused Tricyclic Indoles.
J Org Chem. 2020 08 21; 85(16):10823-10834.JO

Abstract

A novel palladium-catalyzed [2 + 2 + 1] annulation of alkyne-tethered aryl iodides with diaziridinone was developed, leading to the formation of 3,4-fused tricyclic indoles. From a mechanistic standpoint, the formation of fused tricyclic indole scaffolds involved C,C-palladacycles, which were synthesized through the intramolecular reaction of aryl halides and alkynes. The cascade reaction described herein could be carried out with a broad range of substrates and provided various 3,4-fused tricyclic indoles with yields up to 98%.

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Publisher Full Text (DOI)

Authors+Show Affiliations

College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. China.

College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. China.

College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. China.

College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. China.

College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. China.

College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. China.

College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. China.

Pub Type(s)

Journal Article

Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

32786647

Citation

Zhang, Lei, et al. "Palladium-Catalyzed [2 + 2 + 1] Annulation of Alkyne-Tethered Aryl Iodides With Diaziridinone: Synthesis of 3,4-Fused Tricyclic Indoles." The Journal of Organic Chemistry, vol. 85, no. 16, 2020, pp. 10823-10834.

Zhang L, Chen J, Zhong T, et al. Palladium-Catalyzed [2 + 2 + 1] Annulation of Alkyne-Tethered Aryl Iodides with Diaziridinone: Synthesis of 3,4-Fused Tricyclic Indoles. J Org Chem. 2020;85(16):10823-10834.

Zhang, L., Chen, J., Zhong, T., Zheng, X., Zhou, J., Jiang, X., & Yu, C. (2020). Palladium-Catalyzed [2 + 2 + 1] Annulation of Alkyne-Tethered Aryl Iodides with Diaziridinone: Synthesis of 3,4-Fused Tricyclic Indoles. The Journal of Organic Chemistry, 85(16), 10823-10834. https://doi.org/10.1021/acs.joc.0c01365

Zhang L, et al. Palladium-Catalyzed [2 + 2 + 1] Annulation of Alkyne-Tethered Aryl Iodides With Diaziridinone: Synthesis of 3,4-Fused Tricyclic Indoles. J Org Chem. 2020 08 21;85(16):10823-10834. PubMed PMID: 32786647.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Palladium-Catalyzed [2 + 2 + 1] Annulation of Alkyne-Tethered Aryl Iodides with Diaziridinone: Synthesis of 3,4-Fused Tricyclic Indoles. AU - Zhang,Lei, AU - Chen,Junyu, AU - Zhong,Tianshuo, AU - Zheng,Xiangyun, AU - Zhou,Jian, AU - Jiang,Xinpeng, AU - Yu,Chuanming, Y1 - 2020/08/13/ PY - 2020/8/14/pubmed PY - 2020/8/14/medline PY - 2020/8/14/entrez SP - 10823 EP - 10834 JF - The Journal of organic chemistry JO - J Org Chem VL - 85 IS - 16 N2 - A novel palladium-catalyzed [2 + 2 + 1] annulation of alkyne-tethered aryl iodides with diaziridinone was developed, leading to the formation of 3,4-fused tricyclic indoles. From a mechanistic standpoint, the formation of fused tricyclic indole scaffolds involved C,C-palladacycles, which were synthesized through the intramolecular reaction of aryl halides and alkynes. The cascade reaction described herein could be carried out with a broad range of substrates and provided various 3,4-fused tricyclic indoles with yields up to 98%. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/32786647/Palladium_Catalyzed_[2_+_2_+_1]_Annulation_of_Alkyne_Tethered_Aryl_Iodides_with_Diaziridinone:_Synthesis_of_34_Fused_Tricyclic_Indoles_ DB - PRIME DP - Unbound Medicine ER -