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

McNichols, Brett W.; Koubek, Joshua T.; Sellinger, Alan

doi:10.1039/C7CC05909D

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

Journal Article · Fri Oct 27 00:00:00 EDT 2017 · ChemComm

DOI:https://doi.org/10.1039/C7CC05909D· OSTI ID:1409497

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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)

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%).

View Accepted Manuscript (DOE)

Research Organization:: National Renewable Energy Laboratory (NREL), Golden, CO (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE), Solar Energy Technologies Office (EE-4S)

Grant/Contract Number:: AC36-08GO28308

OSTI ID:: 1409497

Report Number(s):: NREL/JA--5900-70539

Journal Information:: ChemComm, Journal Name: ChemComm Journal Issue: 92 Vol. 53; ISSN CHCOFS; ISSN 1359-7345

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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

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