Single-Step Synthesis of Styryl Phosphonic Acids via Palladium-Catalyzed Heck Coupling of Vinyl Phosphonic Acid with Aryl Halides

Alan Sellinger; Brett McNichols; Joshua Koubek

doi:10.1039/C7CC05909D

Single-Step Synthesis of Styryl Phosphonic Acids via Palladium-Catalyzed Heck Coupling of Vinyl Phosphonic Acid with Aryl Halides

Alan Sellinger
, Brett McNichols
, Joshua Koubek

Chemistry and Nanoscience

Research output: Contribution to journal › Article › peer-review

6 Scopus Citations

Abstract

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%).

Original language	American English
Pages (from-to)	12454-12456
Number of pages	3
Journal	Chemical Communications
Volume	53
Issue number	92
DOIs	https://doi.org/10.1039/C7CC05909D
State	Published - 2017

NLR Publication Number

NREL/JA-5900-70539

Keywords

aryl halides
catalysts
phosphonic acids

Access to Document

10.1039/C7CC05909D

Cite this

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title = "Single-Step Synthesis of Styryl Phosphonic Acids via Palladium-Catalyzed Heck Coupling of Vinyl Phosphonic Acid with Aryl Halides",

abstract = "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\%).",

keywords = "aryl halides, catalysts, phosphonic acids",

author = "Alan Sellinger and Brett McNichols and Joshua Koubek",

year = "2017",

doi = "10.1039/C7CC05909D",

language = "American English",

volume = "53",

pages = "12454--12456",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

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T1 - Single-Step Synthesis of Styryl Phosphonic Acids via Palladium-Catalyzed Heck Coupling of Vinyl Phosphonic Acid with Aryl Halides

AU - Sellinger, Alan

AU - McNichols, Brett

AU - Koubek, Joshua

PY - 2017

Y1 - 2017

N2 - 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%).

AB - 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%).

KW - aryl halides

KW - catalysts

KW - phosphonic acids

U2 - 10.1039/C7CC05909D

DO - 10.1039/C7CC05909D

M3 - Article

SN - 1359-7345

VL - 53

SP - 12454

EP - 12456

JO - Chemical Communications

JF - Chemical Communications

IS - 92

ER -

Single-Step Synthesis of Styryl Phosphonic Acids via Palladium-Catalyzed Heck Coupling of Vinyl Phosphonic Acid with Aryl Halides

Abstract

NLR Publication Number

Keywords

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