Synthesis of Tridentate [1,2,4] Triazinyl-Pyridin-2-yl Indole Lewis Basic Complexants via Pd-Catalyzed Suzuki–Miyaura Cross-Coupling

Gulledge, Zachary Z.; Tedder, Mariah L.; Lyons, Kyle R.; Carrick, Jesse D.

doi:10.1021/acsomega.9b02891

Title: Synthesis of Tridentate [1,2,4] Triazinyl-Pyridin-2-yl Indole Lewis Basic Complexants via Pd-Catalyzed Suzuki–Miyaura Cross-Coupling

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Abstract

Full closure of the nuclear fuel cycle is predicated, in part, on defining efficient separations processes for the effective speciation of the neutron-absorbing lanthanides from the minor actinides post-PUREX. Pursuant to the aforementioned, a class of tridentate, Lewis basic procomplexants have been prepared leveraging a Pd-catalyzed Suzuki–Miyaura cross-coupling between 6-bromo-[1,2,4]-triazinylpyridine derivatives and various protected indole-boronic acids to afford functionalized 2-[6-(5,6-diphenyl-[1,2,4]triazin-3-yl)-pyridin-2-yl]-1H-indoles. A highly active catalyst/ligand system with low loadings was employed rapidly affording 26 examples in yields as high as 85%. Method optimization, substrate and indole scope, comparative analysis between coupling reagents, and a scale-up experiment are reported.

Authors:

Gulledge, Zachary Z. ^[1]; Tedder, Mariah L. ^[1]; Lyons, Kyle R. ^[1];

^[1]

Department of Chemistry, Tennessee Technological University, 55 University Drive, Cookeville, Tennessee 38505-0001, United States

Publication Date:: 2019-10-29

Research Org.:: Tennessee Technological Univ., Cookeville, TN (United States)

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF)

OSTI Identifier:: 1572218

Alternate Identifier(s):: OSTI ID: 1574459

Grant/Contract Number:: SC0018033

Resource Type:: Published Article

Journal Name:: ACS Omega

Additional Journal Information:: Journal Name: ACS Omega Journal Volume: 4 Journal Issue: 20; Journal ID: ISSN 2470-1343

Publisher:: American Chemical Society

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats


                    Gulledge, Zachary Z., Tedder, Mariah L., Lyons, Kyle R., and Carrick, Jesse D. Synthesis of Tridentate [1,2,4] Triazinyl-Pyridin-2-yl Indole Lewis Basic Complexants via Pd-Catalyzed Suzuki–Miyaura Cross-Coupling.  United States: N. p., 2019. 
Web.  https://doi.org/10.1021/acsomega.9b02891.

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                    Gulledge, Zachary Z., Tedder, Mariah L., Lyons, Kyle R., & Carrick, Jesse D. Synthesis of Tridentate [1,2,4] Triazinyl-Pyridin-2-yl Indole Lewis Basic Complexants via Pd-Catalyzed Suzuki–Miyaura Cross-Coupling.  United States.  https://doi.org/10.1021/acsomega.9b02891

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                    Gulledge, Zachary Z., Tedder, Mariah L., Lyons, Kyle R., and Carrick, Jesse D. Tue .  
"Synthesis of Tridentate [1,2,4] Triazinyl-Pyridin-2-yl Indole Lewis Basic Complexants via Pd-Catalyzed Suzuki–Miyaura Cross-Coupling".  United States.  https://doi.org/10.1021/acsomega.9b02891.

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@article{osti_1572218,

  title        = {Synthesis of Tridentate [1,2,4] Triazinyl-Pyridin-2-yl Indole Lewis Basic Complexants via Pd-Catalyzed Suzuki–Miyaura Cross-Coupling},

  author       = {Gulledge, Zachary Z. and Tedder, Mariah L. and Lyons, Kyle R. and Carrick, Jesse D.},

  abstractNote = {Full closure of the nuclear fuel cycle is predicated, in part, on defining efficient separations processes for the effective speciation of the neutron-absorbing lanthanides from the minor actinides post-PUREX. Pursuant to the aforementioned, a class of tridentate, Lewis basic procomplexants have been prepared leveraging a Pd-catalyzed Suzuki–Miyaura cross-coupling between 6-bromo-[1,2,4]-triazinylpyridine derivatives and various protected indole-boronic acids to afford functionalized 2-[6-(5,6-diphenyl-[1,2,4]triazin-3-yl)-pyridin-2-yl]-1H-indoles. A highly active catalyst/ligand system with low loadings was employed rapidly affording 26 examples in yields as high as 85%. Method optimization, substrate and indole scope, comparative analysis between coupling reagents, and a scale-up experiment are reported.},

  doi          = {10.1021/acsomega.9b02891},

  journal      = {ACS Omega},

  number       = 20,

  volume       = 4,

  place        = {United States},

  year         = {2019},

  month        = {10}

}

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