skip to main content

DOE PAGESDOE PAGES

Title: Single-step synthesis of styryl phosphonic acids via palladium-catalyzed Heck coupling of vinyl phosphonic acid with aryl halides

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:
ORCiD logo [1] ; ORCiD logo [2] ; ORCiD logo [3]
  1. Colorado School of Mines, Golden, CO (United States). Dept. of Chemistry; United States Air Force Academy, Colorado Springs, CO (United States). Dept. of Chemistry
  2. Colorado School of Mines, Golden, CO (United States). Dept. of Chemistry
  3. 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:
Report Number(s):
NREL/JA-5900-70539
Journal ID: ISSN 1359-7345; CHCOFS
Grant/Contract Number:
AC36-08GO28308
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
Research Org:
National Renewable Energy Lab. (NREL), Golden, CO (United States)
Sponsoring Org:
USDOE Office of Energy Efficiency and Renewable Energy (EERE), Solar Energy Technologies Office (EE-4S)
Country of Publication:
United States
Language:
English
Subject:
09 BIOMASS FUELS; CATALYSTS; ARYL HALIDES; PHOSPHONIC ACIDS
OSTI Identifier:
1409497

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., 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. doi:10.1039/C7CC05909D.
McNichols, Brett W., Koubek, Joshua T., and Sellinger, Alan. 2017. "Single-step synthesis of styryl phosphonic acids via palladium-catalyzed Heck coupling of vinyl phosphonic acid with aryl halides". United States. doi: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}
}

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
  • DOI: 10.1002/anie.198605081