Dimethylisosorbide (DMI) as a bio-derived solvent for Pd-catalyzed cross-coupling reactions

Kirsty L. Wilson; Jane Murray; Helen Sneddon; Craig Jamieson; Allan J. B. Watson

doi:10.1055/s-0037-1611054

Dimethylisosorbide (DMI) as a bio-derived solvent for Pd-catalyzed cross-coupling reactions

Kirsty L. Wilson, Jane Murray, Helen Sneddon, Craig Jamieson, Allan J. B. Watson

School of Chemistry

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Abstract

Palladium-catalyzed bond forming reactions, such as the SuzukiMiyaura and Mizoroki-Heck reactions, are some of the most broadly utilized reactions within the chemical industry. These reactions frequently employ hazardous solvents; however, to adhere to increasing sustainability pressures and restrictions regarding the use of such solvents, alternatives are highly sought after. Here we demonstrate the utility of dimethyl isosorbide (DMI) as a bio-derived solvent in several benchmark Pd-catalysed reactions: Suzuki– Miyaura (13 examples, 62–100% yield), Mizoroki–Heck (13 examples, 47– 91% yield), and Sonogashira (12 examples, 65–98% yield).

Original language	English
Pages (from-to)	2293-2297
Number of pages	5
Journal	Synlett
Volume	29
Issue number	17
Early online date	28 Sept 2018
DOIs	https://doi.org/10.1055/s-0037-1611054
Publication status	Published - Oct 2018

Keywords

Cross-coupling
Green chemistry
Palladium
Solvents

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10.1055/s-0037-1611054

Wilson_2018_Synlett_DMI_AAM
Copyright © 2018 Georg Thieme Verlag Stuttgart, New York. This work has been made available online in accordance with the publisher’s policies. This is the author created accepted version manuscript following peer review and as such may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1055/s-0037-1611054
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title = "Dimethylisosorbide (DMI) as a bio-derived solvent for Pd-catalyzed cross-coupling reactions",

abstract = "Palladium-catalyzed bond forming reactions, such as the SuzukiMiyaura and Mizoroki-Heck reactions, are some of the most broadly utilized reactions within the chemical industry. These reactions frequently employ hazardous solvents; however, to adhere to increasing sustainability pressures and restrictions regarding the use of such solvents, alternatives are highly sought after. Here we demonstrate the utility of dimethyl isosorbide (DMI) as a bio-derived solvent in several benchmark Pd-catalysed reactions: Suzuki– Miyaura (13 examples, 62–100% yield), Mizoroki–Heck (13 examples, 47– 91% yield), and Sonogashira (12 examples, 65–98% yield). ",

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note = "The authors thank the University of Strathclyde for a PhD studentship (KLW) and Merck KGaA, Darmstadt, Germany, for financial and material support.",

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AU - Sneddon, Helen

AU - Jamieson, Craig

AU - Watson, Allan J. B.

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N2 - Palladium-catalyzed bond forming reactions, such as the SuzukiMiyaura and Mizoroki-Heck reactions, are some of the most broadly utilized reactions within the chemical industry. These reactions frequently employ hazardous solvents; however, to adhere to increasing sustainability pressures and restrictions regarding the use of such solvents, alternatives are highly sought after. Here we demonstrate the utility of dimethyl isosorbide (DMI) as a bio-derived solvent in several benchmark Pd-catalysed reactions: Suzuki– Miyaura (13 examples, 62–100% yield), Mizoroki–Heck (13 examples, 47– 91% yield), and Sonogashira (12 examples, 65–98% yield).

AB - Palladium-catalyzed bond forming reactions, such as the SuzukiMiyaura and Mizoroki-Heck reactions, are some of the most broadly utilized reactions within the chemical industry. These reactions frequently employ hazardous solvents; however, to adhere to increasing sustainability pressures and restrictions regarding the use of such solvents, alternatives are highly sought after. Here we demonstrate the utility of dimethyl isosorbide (DMI) as a bio-derived solvent in several benchmark Pd-catalysed reactions: Suzuki– Miyaura (13 examples, 62–100% yield), Mizoroki–Heck (13 examples, 47– 91% yield), and Sonogashira (12 examples, 65–98% yield).

KW - Cross-coupling

KW - Green chemistry

KW - Palladium

KW - Solvents

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Dimethylisosorbide (DMI) as a bio-derived solvent for Pd-catalyzed cross-coupling reactions

Abstract

Keywords

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