Utilizing Glycerol as an Ex Situ CO-source in Pd-Catalyzed Alkoxycarbonylation of Styrenes

Dorrit Bolund Nielsen; Benjamin  Wahlqvist; Dennis Ulsøe Nielsen; Kim Daasbjerg; Troels Skrydstrup

doi:10.1021/acscatal.7b02179

Utilizing Glycerol as an Ex Situ CO-source in Pd-Catalyzed Alkoxycarbonylation of Styrenes

Dorrit Bolund Nielsen, Benjamin Wahlqvist, Dennis Ulsøe Nielsen, Kim Daasbjerg, Troels Skrydstrup

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

29 Citations (Scopus)

Abstract

We report on an efficient Ir-catalyzed decarbon-ylation of glycerol, which could be coupled to an ensuing Pd-catalyzed alkoxycarbonylation of styrenes. The formation of hydrogen could be avoided by employing 1,4-benzoquinone (BQ) as an external oxidant. A wide variety of styrenes underwent the esterification in good yields and high regioselectivity. Applying catalytic amounts of hexafluoroiso-propanol provided access to alcohols other than methanol, which this transformation is often limited to. Finally, we demonstrate the suitability of this methodology for the preparation of three well-known nonsteroidal anti-inflammatory drugs (NSAIDs).

Original language	English
Journal	ACS Catalysis
Volume	7
Issue	9
Pages (from-to)	6089–6093
Number of pages	5
ISSN	2155-5435
DOIs	https://doi.org/10.1021/acscatal.7b02179
Publication status	Published - 10 Aug 2017

Keywords

Carbon monoxide
Catalysis
Esters
Glycerol
Palladium
Styrenes

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10.1021/acscatal.7b02179

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title = "Utilizing Glycerol as an Ex Situ CO-source in Pd-Catalyzed Alkoxycarbonylation of Styrenes",

abstract = "We report on an efficient Ir-catalyzed decarbon-ylation of glycerol, which could be coupled to an ensuing Pd-catalyzed alkoxycarbonylation of styrenes. The formation of hydrogen could be avoided by employing 1,4-benzoquinone (BQ) as an external oxidant. A wide variety of styrenes underwent the esterification in good yields and high regioselectivity. Applying catalytic amounts of hexafluoroiso-propanol provided access to alcohols other than methanol, which this transformation is often limited to. Finally, we demonstrate the suitability of this methodology for the preparation of three well-known nonsteroidal anti-inflammatory drugs (NSAIDs).",

keywords = "Carbon monoxide, Catalysis, Esters, Glycerol, Palladium, Styrenes",

author = "Nielsen, {Dorrit Bolund} and Benjamin Wahlqvist and Nielsen, {Dennis Uls{\o}e} and Kim Daasbjerg and Troels Skrydstrup",

year = "2017",

month = aug,

day = "10",

doi = "10.1021/acscatal.7b02179",

language = "English",

volume = "7",

pages = "6089–6093",

journal = "ACS Catalysis",

issn = "2155-5435",

publisher = "American Chemical Society",

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Utilizing Glycerol as an Ex Situ CO-source in Pd-Catalyzed Alkoxycarbonylation of Styrenes. / Nielsen, Dorrit Bolund; Wahlqvist, Benjamin ; Nielsen, Dennis Ulsøe et al.
In: ACS Catalysis, Vol. 7, No. 9, 10.08.2017, p. 6089–6093.

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

TY - JOUR

T1 - Utilizing Glycerol as an Ex Situ CO-source in Pd-Catalyzed Alkoxycarbonylation of Styrenes

AU - Nielsen, Dorrit Bolund

AU - Wahlqvist, Benjamin

AU - Nielsen, Dennis Ulsøe

AU - Daasbjerg, Kim

AU - Skrydstrup, Troels

PY - 2017/8/10

Y1 - 2017/8/10

N2 - We report on an efficient Ir-catalyzed decarbon-ylation of glycerol, which could be coupled to an ensuing Pd-catalyzed alkoxycarbonylation of styrenes. The formation of hydrogen could be avoided by employing 1,4-benzoquinone (BQ) as an external oxidant. A wide variety of styrenes underwent the esterification in good yields and high regioselectivity. Applying catalytic amounts of hexafluoroiso-propanol provided access to alcohols other than methanol, which this transformation is often limited to. Finally, we demonstrate the suitability of this methodology for the preparation of three well-known nonsteroidal anti-inflammatory drugs (NSAIDs).

AB - We report on an efficient Ir-catalyzed decarbon-ylation of glycerol, which could be coupled to an ensuing Pd-catalyzed alkoxycarbonylation of styrenes. The formation of hydrogen could be avoided by employing 1,4-benzoquinone (BQ) as an external oxidant. A wide variety of styrenes underwent the esterification in good yields and high regioselectivity. Applying catalytic amounts of hexafluoroiso-propanol provided access to alcohols other than methanol, which this transformation is often limited to. Finally, we demonstrate the suitability of this methodology for the preparation of three well-known nonsteroidal anti-inflammatory drugs (NSAIDs).

KW - Carbon monoxide

KW - Catalysis

KW - Esters

KW - Glycerol

KW - Palladium

KW - Styrenes

U2 - 10.1021/acscatal.7b02179

DO - 10.1021/acscatal.7b02179

M3 - Journal article

SN - 2155-5435

VL - 7

SP - 6089

EP - 6093

JO - ACS Catalysis

JF - ACS Catalysis

IS - 9

ER -

Utilizing Glycerol as an Ex Situ CO-source in Pd-Catalyzed Alkoxycarbonylation of Styrenes

Abstract

Keywords

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