DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Convergent access to bis-1,2,4-triazinyl-2,2′-bipyridines (BTBPs) and 2,2′-bipyridines via a Pd-catalyzed Ullman-type reaction


Access to functionalized BTBP complexants through a reductive coupling strategy decreases linearity of common synthetic strategies towards these relevant materials for separations.

ORCiD logo [1]; ORCiD logo [1]
  1. Department of Chemistry, Tennessee Technological University, Cookeville, USA
Publication Date:
Research Org.:
Tennessee Technological Univ., Cookeville, TN (United States)
Sponsoring Org.:
USDOE Office of Science (SC)
OSTI Identifier:
Alternate Identifier(s):
OSTI ID: 1803231
Grant/Contract Number:  
Resource Type:
Published Article
Journal Name:
RSC Advances
Additional Journal Information:
Journal Name: RSC Advances Journal Volume: 10 Journal Issue: 18; Journal ID: ISSN 2046-2069
Royal Society of Chemistry (RSC)
Country of Publication:
United Kingdom

Citation Formats

Waters, Gabrielle D., and Carrick, Jesse D. Convergent access to bis-1,2,4-triazinyl-2,2′-bipyridines (BTBPs) and 2,2′-bipyridines via a Pd-catalyzed Ullman-type reaction. United Kingdom: N. p., 2020. Web. doi:10.1039/D0RA00673D.
Waters, Gabrielle D., & Carrick, Jesse D. Convergent access to bis-1,2,4-triazinyl-2,2′-bipyridines (BTBPs) and 2,2′-bipyridines via a Pd-catalyzed Ullman-type reaction. United Kingdom.
Waters, Gabrielle D., and Carrick, Jesse D. Mon . "Convergent access to bis-1,2,4-triazinyl-2,2′-bipyridines (BTBPs) and 2,2′-bipyridines via a Pd-catalyzed Ullman-type reaction". United Kingdom.
title = {Convergent access to bis-1,2,4-triazinyl-2,2′-bipyridines (BTBPs) and 2,2′-bipyridines via a Pd-catalyzed Ullman-type reaction},
author = {Waters, Gabrielle D. and Carrick, Jesse D.},
abstractNote = {Access to functionalized BTBP complexants through a reductive coupling strategy decreases linearity of common synthetic strategies towards these relevant materials for separations.},
doi = {10.1039/D0RA00673D},
journal = {RSC Advances},
number = 18,
volume = 10,
place = {United Kingdom},
year = {2020},
month = {3}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record

Save / Share:

Works referenced in this record:

Synthesis of cis -/All- cis -Substituted Cyclopropanes through Stereocontrolled Metalation and Pd-Catalyzed Negishi Coupling
journal, November 2018

Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C–C Bonds
journal, July 2015

Substituted 2,2′-Bipyridines by Nickel Catalysis: 4,4′-Di-tert-butyl-2,2′-bipyridine
journal, August 2013

Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis
journal, March 2013

  • Prier, Christopher K.; Rankic, Danica A.; MacMillan, David W. C.
  • Chemical Reviews, Vol. 113, Issue 7
  • DOI: 10.1021/cr300503r

NMR Chemical Shifts of Trace Impurities: Common Laboratory Solvents, Organics, and Gases in Deuterated Solvents Relevant to the Organometallic Chemist
journal, May 2010

  • Fulmer, Gregory R.; Miller, Alexander J. M.; Sherden, Nathaniel H.
  • Organometallics, Vol. 29, Issue 9
  • DOI: 10.1021/om100106e

LiPF 6 Stabilizer and Transition-Metal Cation Scavenger: A Bifunctional Bipyridine-Based Ligand for Lithium-Ion Battery Application
journal, May 2019

Palladium and TEMPO as Co-Catalysts in a Desulfinative Homocoupling Reaction: Palladium and TEMPO as Co-Catalysts in Homocoupling
journal, April 2014

  • Ortgies, Dirk H.; Chen, Fei; Forgione, Pat
  • European Journal of Organic Chemistry, Vol. 2014, Issue 18
  • DOI: 10.1002/ejoc.201402134

First-Row Transition Metal (De)Hydrogenation Catalysis Based On Functional Pincer Ligands
journal, October 2018

From BTBPs to BTPhens: The Effect of Ligand Pre-Organization on the Extraction Properties of Quadridentate Bis-Triazine Ligands
journal, January 2012

Copper-Mediated Coupling Reactions and Their Applications in Natural Products and Designed Biomolecules Synthesis
journal, August 2008

  • Evano, Gwilherm; Blanchard, Nicolas; Toumi, Mathieu
  • Chemical Reviews, Vol. 108, Issue 8
  • DOI: 10.1021/cr8002505

Aryl−Aryl Bond Formation One Century after the Discovery of the Ullmann Reaction
journal, May 2002

  • Hassan, Jwanro; Sévignon, Marc; Gozzi, Christel
  • Chemical Reviews, Vol. 102, Issue 5, p. 1359-1470
  • DOI: 10.1021/cr000664r

Catalytic homocoupling of aryl, alkenyl, and alkynyl halides with Ni(II)-complexes and zirconocene dichloride
journal, April 2011

Recognition of Some Lanthanides, Actinides, and Transition- and Heavy-Metal Cations by N-Donor Ligands: Thermodynamic and Kinetic Aspects
journal, February 2010

  • Hubscher-Bruder, Véronique; Haddaoui, Jaouad; Bouhroum, Saliha
  • Inorganic Chemistry, Vol. 49, Issue 4
  • DOI: 10.1021/ic9010899

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

Kumada Coupling of Aryl, Heteroaryl, and Vinyl Chlorides Catalyzed by Amido Pincer Nickel Complexes
journal, December 2011

  • Liu, Ning; Wang, Zhong-Xia
  • The Journal of Organic Chemistry, Vol. 76, Issue 24
  • DOI: 10.1021/jo201821g

Phosphonate-Based Bipyridine Dyes for Stable Photovoltaic Devices
journal, November 2001

  • Gillaizeau-Gauthier, Isabelle; Odobel, Fabrice; Alebbi, Monica
  • Inorganic Chemistry, Vol. 40, Issue 23
  • DOI: 10.1021/ic010192e

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

  • Martin, Ruben; Buchwald, Stephen L.
  • Accounts of Chemical Research, Vol. 41, Issue 11
  • DOI: 10.1021/ar800036s

[(CyPF- t Bu)PdCl 2 ]: An Air-Stable, One-Component, Highly Efficient Catalyst for Amination of Heteroaryl and Aryl Halides
journal, September 2008

  • Shen, Qilong; Hartwig, John F.
  • Organic Letters, Vol. 10, Issue 18
  • DOI: 10.1021/ol801615u

A practical cobalt-catalyzed cross-coupling of benzylic zinc reagents with aryl and heteroaryl bromides or chlorides
journal, January 2016

  • Benischke, Andreas D.; Knoll, Irina; Rérat, Alice
  • Chemical Communications, Vol. 52, Issue 15
  • DOI: 10.1039/C5CC10272C

Lanthanide Speciation in Potential SANEX and GANEX Actinide/Lanthanide Separations Using Tetra-N-Donor Extractants
journal, June 2012

  • Whittaker, Daniel M.; Griffiths, Tamara L.; Helliwell, Madeleine
  • Inorganic Chemistry, Vol. 52, Issue 7
  • DOI: 10.1021/ic301599y

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

Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners
journal, March 2011

  • Jana, Ranjan; Pathak, Tejas P.; Sigman, Matthew S.
  • Chemical Reviews, Vol. 111, Issue 3
  • DOI: 10.1021/cr100327p

Trivalent Actinide and Lanthanide Separations by Tetradentate Nitrogen Ligands: A Quantum Chemistry Study
journal, October 2011

  • Lan, Jian-Hui; Shi, Wei-Qun; Yuan, Li-Yong
  • Inorganic Chemistry, Vol. 50, Issue 19
  • DOI: 10.1021/ic200078j

Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions
journal, September 2016

Cobalt-Catalyzed Reductive Cross-Coupling Between Styryl and Benzyl Halides
journal, December 2016

  • Cai, Yingxiao; Benischke, Andreas D.; Knochel, Paul
  • Chemistry - A European Journal, Vol. 23, Issue 2
  • DOI: 10.1002/chem.201603832

Pd-Catalyzed Diamination of 1,2,4-Triazinyl Complexant Scaffolds
journal, June 2015

  • Tai, Serene; Dover, Evan J.; Marchi, Sydney V.
  • The Journal of Organic Chemistry, Vol. 80, Issue 12
  • DOI: 10.1021/acs.joc.5b00710

Efficient Preparation of Pyridinyl-1,2,4-Triazines via Telescoped Condensation with Diversely Functionalized 1,2-Dicarbonyls: Pyridinyl 1,2,4-Triazines
journal, July 2015

  • Tai, Serene; Marchi, Sydney V.; Carrick, Jesse D.
  • Journal of Heterocyclic Chemistry, Vol. 53, Issue 4
  • DOI: 10.1002/jhet.2374

New ligands for nickel catalysis from diverse pharmaceutical heterocycle libraries
journal, August 2016

  • Hansen, Eric C.; Pedro, Dylan J.; Wotal, Alexander C.
  • Nature Chemistry, Vol. 8, Issue 12
  • DOI: 10.1038/nchem.2587

journal, January 1999

  • Kolarik, Zdenek; Müllich, Udo; Gassner, Franz
  • Solvent Extraction and Ion Exchange, Vol. 17, Issue 1
  • DOI: 10.1080/07360299908934598

Computational Explorations of Mechanisms and Ligand-Directed Selectivities of Copper-Catalyzed Ullmann-Type Reactions
journal, May 2010

  • Jones, Gavin O.; Liu, Peng; Houk, K. N.
  • Journal of the American Chemical Society, Vol. 132, Issue 17
  • DOI: 10.1021/ja100739h

Bipyridine:  The Most Widely Used Ligand. A Review of Molecules Comprising at Least Two 2,2‘-Bipyridine Units
journal, October 2000

  • Kaes, Christian; Katz, Alexander; Hosseini, Mir Wais
  • Chemical Reviews, Vol. 100, Issue 10
  • DOI: 10.1021/cr990376z

Characterization of Lanthanide Complexes with Bis-1,2,3-triazole-bipyridine Ligands Involved in Actinide/Lanthanide Separation
journal, October 2016

journal, September 1999

  • Kolarik, Zdenek; Mullich, Udo; Gassner, Franz
  • Solvent Extraction and Ion Exchange, Vol. 17, Issue 5
  • DOI: 10.1080/07366299908934641

4,4′,4″-Trimethyl-2,2′:6′,2″-terpyridine by Oxidative Coupling of 4-Picoline
journal, October 2014

  • Robo, Michael T.; Prinsell, Michael R.; Weix, Daniel J.
  • The Journal of Organic Chemistry, Vol. 79, Issue 21
  • DOI: 10.1021/jo501925s

Multicoordinate ligands for actinide/lanthanide separations
journal, January 2007

  • Dam, Henk H.; Reinhoudt, David N.; Verboom, Willem
  • Chem. Soc. Rev., Vol. 36, Issue 2
  • DOI: 10.1039/B603847F

Rapid Synthesis of Boc-2′,6′-dimethyl- l -tyrosine and Derivatives and Incorporation into Opioid Peptidomimetics
journal, October 2015

Synthesis of Tridentate [1,2,4] Triazinyl-Pyridin-2-yl Indole Lewis Basic Complexants via Pd-Catalyzed Suzuki–Miyaura Cross-Coupling
journal, October 2019

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

  • Gottlieb, Hugo E.; Kotlyar, Vadim; Nudelman, Abraham
  • The Journal of Organic Chemistry, Vol. 62, Issue 21
  • DOI: 10.1021/jo971176v

Improved synthesis of electron deficient bipyridines
journal, May 2016

The Halogen/Magnesium-Exchange Using iPrMgCl·LiCl and Related Exchange Reagents
journal, January 2014

  • Knochel, Paul; M. Barl, Nadja; Werner, Veronika
  • HETEROCYCLES, Vol. 88, Issue 2
  • DOI: 10.3987/REV-13-SR(S)4

Highly Reactive, General, and Long-Lived Catalysts for Coupling Heteroaryl and Aryl Chlorides with Primary Nitrogen Nucleophiles
journal, February 2005

  • Shen, Qilong; Shekhar, Shashank; Stambuli, James P.
  • Angewandte Chemie International Edition, Vol. 44, Issue 9
  • DOI: 10.1002/anie.200462629

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

  • Chaudhuri, Sauradip; Carrick, Jesse D.
  • The Journal of Organic Chemistry, Vol. 83, Issue 17
  • DOI: 10.1021/acs.joc.8b01446

Uranyl Complexes with Aroylbis( N , N -dialkylthioureas)
journal, September 2018

A Warning on the Use of Radical Traps as a Test for Radical Mechanisms:  They React with Palladium Hydrido Complexes
journal, September 2002

  • Albéniz, Ana C.; Espinet, Pablo; López-Fernández, Raquel
  • Journal of the American Chemical Society, Vol. 124, Issue 38
  • DOI: 10.1021/ja0271126

Copper-Mediated C–H Activation/C–S Cross-Coupling of Heterocycles with Thiols
journal, November 2011

  • Ranjit, Sadananda; Lee, Richmond; Heryadi, Dodi
  • The Journal of Organic Chemistry, Vol. 76, Issue 21
  • DOI: 10.1021/jo2017444

Recent advancement of Ullmann-type coupling reactions in the formation of C–C bond
journal, October 2016

Remarkable Tuning of the Coordination and Photophysical Properties of Lanthanide Ions in a Series of Tetrazole-Based Complexes
journal, September 2009

  • Andreiadis, Eugen S.; Demadrille, Renaud; Imbert, Daniel
  • Chemistry - A European Journal, Vol. 15, Issue 37
  • DOI: 10.1002/chem.200900912

Synthesis of Solid 2-Pyridylzinc Reagents and Their Application in Negishi Reactions
journal, October 2013

  • Colombe, James R.; Bernhardt, Sebastian; Stathakis, Christos
  • Organic Letters, Vol. 15, Issue 22
  • DOI: 10.1021/ol402798z

Reductive Couplings of 2-Halopyridines without External Ligand: Phosphine-Free Nickel-Catalyzed Synthesis of Symmetrical and Unsymmetrical 2,2′-Bipyridines
journal, December 2013

  • Liao, Lian-Yan; Kong, Xing-Rui; Duan, Xin-Fang
  • The Journal of Organic Chemistry, Vol. 79, Issue 2
  • DOI: 10.1021/jo402084m