Single-step synthesis of styryl phosphonic acids via palladium-catalyzed Heck coupling of vinyl phosphonic acid with aryl halides
Abstract
Here, we have developed a single step palladium-catalyzed Heck coupling of aryl halides with vinyl phosphonic acid to produce functionalized (E)-styryl phosphonic acids. This pathway utilizes a variety of commercially available aryl halides, vinyl phosphonic acid and Pd(P(tBu)3)2 as catalyst. These conditions produce a wide range of styryl phosphonic acids with high purities and good to excellent yields (31–80%).
- Authors:
-
[1];
[2];
[3]
- Colorado School of Mines, Golden, CO (United States). Dept. of Chemistry; United States Air Force Academy, Colorado Springs, CO (United States). Dept. of Chemistry
- Colorado School of Mines, Golden, CO (United States). Dept. of Chemistry
- Colorado School of Mines, Golden, CO (United States). Dept. of Chemistry; Colorado School of Mines, Golden, CO (United States). Materials Science Program; National Renewable Energy Lab. (NREL), Golden, CO (United States)
- Publication Date:
- Research Org.:
- National Renewable Energy Lab. (NREL), Golden, CO (United States)
- Sponsoring Org.:
- USDOE Office of Energy Efficiency and Renewable Energy (EERE), Renewable Power Office. Solar Energy Technologies Office
- OSTI Identifier:
- 1409497
- Report Number(s):
- NREL/JA-5900-70539
Journal ID: ISSN 1359-7345; CHCOFS
- Grant/Contract Number:
- AC36-08GO28308
- Resource Type:
- Accepted Manuscript
- Journal Name:
- ChemComm
- Additional Journal Information:
- Journal Volume: 53; Journal Issue: 92; Journal ID: ISSN 1359-7345
- Publisher:
- Royal Society of Chemistry
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 09 BIOMASS FUELS; CATALYSTS; ARYL HALIDES; PHOSPHONIC ACIDS
Citation Formats
McNichols, Brett W., Koubek, Joshua T., and Sellinger, Alan. Single-step synthesis of styryl phosphonic acids via palladium-catalyzed Heck coupling of vinyl phosphonic acid with aryl halides. United States: N. p., 2017.
Web. doi:10.1039/C7CC05909D.
McNichols, Brett W., Koubek, Joshua T., & Sellinger, Alan. Single-step synthesis of styryl phosphonic acids via palladium-catalyzed Heck coupling of vinyl phosphonic acid with aryl halides. United States. https://doi.org/10.1039/C7CC05909D
McNichols, Brett W., Koubek, Joshua T., and Sellinger, Alan. Fri .
"Single-step synthesis of styryl phosphonic acids via palladium-catalyzed Heck coupling of vinyl phosphonic acid with aryl halides". United States. https://doi.org/10.1039/C7CC05909D. https://www.osti.gov/servlets/purl/1409497.
@article{osti_1409497,
title = {Single-step synthesis of styryl phosphonic acids via palladium-catalyzed Heck coupling of vinyl phosphonic acid with aryl halides},
author = {McNichols, Brett W. and Koubek, Joshua T. and Sellinger, Alan},
abstractNote = {Here, we have developed a single step palladium-catalyzed Heck coupling of aryl halides with vinyl phosphonic acid to produce functionalized (E)-styryl phosphonic acids. This pathway utilizes a variety of commercially available aryl halides, vinyl phosphonic acid and Pd(P(tBu)3)2 as catalyst. These conditions produce a wide range of styryl phosphonic acids with high purities and good to excellent yields (31–80%).},
doi = {10.1039/C7CC05909D},
journal = {ChemComm},
number = 92,
volume = 53,
place = {United States},
year = {2017},
month = {10}
}
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Works referenced in this record:
The Palladium-Catalyzed Cross-Coupling Reactions of Organotin Reagents with Organic Electrophiles [New Synthetic Methods(58)]
journal, June 1986
- Stille, John K.
- Angewandte Chemie International Edition in English, Vol. 25, Issue 6, p. 508-524
Heck Reactions in the Presence of P( t -Bu) 3 : Expanded Scope and Milder Reaction Conditions for the Coupling of Aryl Chlorides
journal, January 1999
- Littke, Adam F.; Fu, Gregory C.
- The Journal of Organic Chemistry, Vol. 64, Issue 1
Review on Modern Advances of Chemical Methods for the Introduction of a Phosphonic Acid Group
journal, December 2011
- Demmer, Charles S.; Krogsgaard-Larsen, Niels; Bunch, Lennart
- Chemical Reviews, Vol. 111, Issue 12
Efficient and Selective Nickel-Catalyzed Addition of H−P(O) and H−S Bonds to Alkynes
journal, April 2004
- Han, Li-Biao; Zhang, Chen; Yazawa, Hideaki
- Journal of the American Chemical Society, Vol. 126, Issue 16
A Versatile Catalyst for Heck Reactions of Aryl Chlorides and Aryl Bromides under Mild Conditions
journal, July 2001
- Littke, Adam F.; Fu, Gregory C.
- Journal of the American Chemical Society, Vol. 123, Issue 29
Tailoring the work function of indium tin oxide electrodes in electrophosphorescent organic light-emitting diodes
journal, April 2009
- Sharma, Asha; Hotchkiss, Peter J.; Marder, Seth R.
- Journal of Applied Physics, Vol. 105, Issue 8
Hydrophobic Organic Hole Transporters for Improved Moisture Resistance in Metal Halide Perovskite Solar Cells
journal, February 2016
- Leijtens, Tomas; Giovenzana, Tommaso; Habisreutinger, Severin N.
- ACS Applied Materials & Interfaces, Vol. 8, Issue 9
Tuning colloidal quantum dot band edge positions through solution-phase surface chemistry modification
journal, May 2017
- Kroupa, Daniel M.; Vörös, Márton; Brawand, Nicholas P.
- Nature Communications, Vol. 8, Issue 1
Surface Modification Using Phosphonic Acids and Esters
journal, April 2012
- Queffélec, Clémence; Petit, Marc; Janvier, Pascal
- Chemical Reviews, Vol. 112, Issue 7
Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides
journal, July 1972
- Heck, R. F.; Nolley, J. P.
- The Journal of Organic Chemistry, Vol. 37, Issue 14
Nickel-Catalyzed Decarboxylative C–P Cross-Coupling of Alkenyl Acids with P(O)H Compounds
journal, August 2014
- Wu, Yile; Liu, Liu; Yan, Kaili
- The Journal of Organic Chemistry, Vol. 79, Issue 17
The surface science of titanium dioxide
journal, January 2003
- Diebold, Ulrike
- Surface Science Reports, Vol. 48, Issue 5-8
Transition-Metal-Catalyzed Oxidative Heck Reactions
journal, April 2010
- Karimi, Babak; Behzadnia, Hesam; Elhamifar, Dawood
- Synthesis, Vol. 2010, Issue 09
The Heck Reaction as a Sharpening Stone of Palladium Catalysis
journal, August 2000
- Beletskaya, Irina P.; Cheprakov, Andrei V.
- Chemical Reviews, Vol. 100, Issue 8
Synthesis of substituted cinnamic acids and cinnamonitriles via palladium catalyzed coupling reactions of aryl halides with acrylic acid and acrylonitrile in aqueous media
journal, August 1989
- Bumagin, N. A.; More, P. G.; Beletskaya, I. P.
- Journal of Organometallic Chemistry, Vol. 371, Issue 3
Conjugated Phosphonic Acid Modified Zinc Oxide Electron Transport Layers for Improved Performance in Organic Solar Cells
journal, October 2014
- Braid, Jennifer L.; Koldemir, Unsal; Sellinger, Alan
- ACS Applied Materials & Interfaces, Vol. 6, Issue 21
Soluble PPVs with Enhanced Performance—A Mechanistic Approach
journal, January 2000
- Becker, H.; Spreitzer, H.; Kreuder, W.
- Advanced Materials, Vol. 12, Issue 1
Microwave-Assisted Palladium-Catalyzed Cross-Coupling of Aryl and Vinyl Halides with H-Phosphonate Diesters
journal, October 2008
- Kalek, Marcin; Ziadi, Asraa; Stawinski, Jacek
- Organic Letters, Vol. 10, Issue 20
Orientation of Phenylphosphonic Acid Self-Assembled Monolayers on a Transparent Conductive Oxide: A Combined NEXAFS, PM-IRRAS, and DFT Study
journal, February 2013
- Gliboff, Matthew; Sang, Lingzi; Knesting, Kristina M.
- Langmuir, Vol. 29, Issue 7
Covalent Surface Modification of Oxide Surfaces
journal, May 2014
- Pujari, Sidharam P.; Scheres, Luc; Marcelis, Antonius T. M.
- Angewandte Chemie International Edition, Vol. 53, Issue 25
Transparent Conducting Oxides in the ZnO-In 2 O 3 -SnO 2 System
journal, June 2010
- Hoel, Cathleen A.; Mason, Thomas O.; Gaillard, Jean-François
- Chemistry of Materials, Vol. 22, Issue 12
Distance dependence of electron transfer rates in bilayers of a ferrocene Langmuir-Blodgett monolayer and a self-assembled monolayer on gold
journal, May 1995
- Guo, Liang-Hong; Facci, John S.; McLendon, George
- The Journal of Physical Chemistry, Vol. 99, Issue 21
Molecular Design for Tuning Work Functions of Transparent Conducting Electrodes
journal, June 2015
- Koldemir, Unsal; Braid, Jennifer L.; Morgenstern, Amanda
- The Journal of Physical Chemistry Letters, Vol. 6, Issue 12
Phosphonic Acids for Interfacial Engineering of Transparent Conductive Oxides
journal, May 2016
- Paniagua, Sergio A.; Giordano, Anthony J.; Smith, O’Neil L.
- Chemical Reviews, Vol. 116, Issue 12