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

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

Abstract

Citation Formats

Indoles in Multicomponent Processes (MCPs) journal, March 2012

Chromatographic separation of Am and Cm journal, February 2011

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journal, June 2013

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journal, May 2009

Complexation and Extraction of Trivalent Actinides and Lanthanides by Triazinylpyridine N -Donor Ligands
journal, October 2012

SELECTIVE EXTRACTION OF Am(III) OVER Eu(III) BY 2,6-DITRIAZOLYL- AND 2,6-DITRIAZINYLPYRIDINES1
journal, January 1999

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Arylboronic Acids and Arylpinacolboronate Esters in Suzuki Coupling Reactions Involving Indoles. Partner Role Swapping and Heterocycle Protection
journal, October 2004

EXTRACTION OF Am(lll) AND Eu(lll) NITRATES BY 2-6-DI-(5,6-DIPROPYL-1,2,4-TRIAZIN-3-YL)PYRIDINES 1
journal, September 1999

Organic Material Based Fluorescent Sensor for Hg2+: a Brief Review on Recent Development
journal, September 2016

NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities
journal, October 1997

Complexation and Separation of Lanthanides(III) and Actinides(III) by Heterocyclic N-Donors in Solutions
journal, October 2008

The preparation of certain new diphenyl and bis(2-pyridyl) as -triazines
journal, June 1968

Organotrifluoroborates: Protected Boronic Acids That Expand the Versatility of the Suzuki Coupling Reaction
journal, January 2007

General Method for Synthesis of 2-Heterocyclic N -Methyliminodiacetic Acid Boronates
journal, April 2010

Pd-Catalyzed Intermolecular Amidation of Aryl Halides: The Discovery that Xantphos Can Be Trans-Chelating in a Palladium Complex
journal, May 2002

Organotrifluoroborates and Monocoordinated Palladium Complexes as CatalystsâA Perfect Combination for SuzukiâMiyaura Coupling
journal, November 2009

Indole alkaloid marine natural products: An established source of cancer drug leads with considerable promise for the control of parasitic, neurological and other diseases
journal, December 2005

Palladium-Catalyzed Suzuki−Miyaura Cross-Coupling Reactions Employing Dialkylbiaryl Phosphine Ligands
journal, November 2008

Bite angle effects of diphosphines in C–C and C–X bond forming cross coupling reactions
journal, January 2009

Modular Approaches to Diversified Soft Lewis Basic Complexants through Suzuki–Miyaura Cross-Coupling of Bromoheteroarenes with Organotrifluoroborates
journal, December 2015

Suzuki-Miyaura Cross-Coupling of Unprotected, Nitrogen-Rich Heterocycles: Substrate Scope and Mechanistic Investigation
journal, August 2013

Synthetic Access to Functionalized Dipolarophiles of Lewis Basic Complexant Scaffolds through Sonogashira Cross-Coupling
journal, July 2018

Mushroom-Derived Indole Alkaloids
journal, June 2017

The synthesis of novel heteroaryl-fused 7,8,9,10-tetrahydro-6H-azepino[1,2-a]indoles, 4-oxo-2,3-dihydro-1H-[1,4]diazepino[1,7-a]indoles and 1,2,4,5-tetrahydro-[1,4]oxazepino[4,5-a]indoles. Effective inhibitors of HCV NS5B polymerase
journal, January 2011

π‐Conjugated Indole Dyads with Strong Blue Emission Made Possible by Stille Cross‐Coupling and Double Fischer Indole Cyclisation
journal, March 2017

Selective Extraction of Am(III) from PUREX Raffinate: The AmSel System
journal, December 2015

Pd-Catalyzed Amination of Functionalized 6-Bromo-pyridinyl-1,2,4-triazine Complexant Scaffolds: Pd-Catalyzed Amination of Functionalized 6-Bromo-pyridinyl-1,2,4-triazine Complexant Scaffolds
journal, June 2017

Synthesis of N-Heterocycles by Reductive Cyclization of Nitro Compounds using Formate Esters as Carbon Monoxide Surrogates
journal, November 2017

Separation of americium from europium using 3,3′-dimethoxy-phenyl-bis-1,2,4-triazinyl-2,6-pyridine
journal, March 2017

A review on recent developments of indole-containing antiviral agents
journal, January 2015