Skip to content

Research at St Andrews

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

Research output: Contribution to journalArticlepeer-review

Standard

Dimethylisosorbide (DMI) as a bio-derived solvent for Pd-catalyzed cross-coupling reactions. / Wilson, Kirsty L.; Murray, Jane; Sneddon, Helen; Jamieson, Craig; Watson, Allan J. B.

In: Synlett, Vol. 29, No. 17, 10.2018, p. 2293-2297.

Research output: Contribution to journalArticlepeer-review

Harvard

Wilson, KL, Murray, J, Sneddon, H, Jamieson, C & Watson, AJB 2018, 'Dimethylisosorbide (DMI) as a bio-derived solvent for Pd-catalyzed cross-coupling reactions', Synlett, vol. 29, no. 17, pp. 2293-2297. https://doi.org/10.1055/s-0037-1611054

APA

Wilson, K. L., Murray, J., Sneddon, H., Jamieson, C., & Watson, A. J. B. (2018). Dimethylisosorbide (DMI) as a bio-derived solvent for Pd-catalyzed cross-coupling reactions. Synlett, 29(17), 2293-2297. https://doi.org/10.1055/s-0037-1611054

Vancouver

Wilson KL, Murray J, Sneddon H, Jamieson C, Watson AJB. Dimethylisosorbide (DMI) as a bio-derived solvent for Pd-catalyzed cross-coupling reactions. Synlett. 2018 Oct;29(17):2293-2297. https://doi.org/10.1055/s-0037-1611054

Author

Wilson, Kirsty L. ; Murray, Jane ; Sneddon, Helen ; Jamieson, Craig ; Watson, Allan J. B. / Dimethylisosorbide (DMI) as a bio-derived solvent for Pd-catalyzed cross-coupling reactions. In: Synlett. 2018 ; Vol. 29, No. 17. pp. 2293-2297.

Bibtex - Download

@article{8f83a73d8767423eab996c7fa62940dd,
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). ",
keywords = "Cross-coupling, Green chemistry, Palladium, Solvents",
author = "Wilson, {Kirsty L.} and Jane Murray and Helen Sneddon and Craig Jamieson and Watson, {Allan J. B.}",
note = "The authors thank the University of Strathclyde for a PhD studentship (KLW) and Merck KGaA, Darmstadt, Germany, for financial and material support.",
year = "2018",
month = oct,
doi = "10.1055/s-0037-1611054",
language = "English",
volume = "29",
pages = "2293--2297",
journal = "Synlett",
issn = "0936-5214",
publisher = "Georg Thieme Verlag",
number = "17",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - Dimethylisosorbide (DMI) as a bio-derived solvent for Pd-catalyzed cross-coupling reactions

AU - Wilson, Kirsty L.

AU - Murray, Jane

AU - Sneddon, Helen

AU - Jamieson, Craig

AU - Watson, Allan J. B.

N1 - The authors thank the University of Strathclyde for a PhD studentship (KLW) and Merck KGaA, Darmstadt, Germany, for financial and material support.

PY - 2018/10

Y1 - 2018/10

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

U2 - 10.1055/s-0037-1611054

DO - 10.1055/s-0037-1611054

M3 - Article

VL - 29

SP - 2293

EP - 2297

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 17

ER -

Related by author

  1. Boron complexes in organic synthesis

    Israel, E. M., Fyfe, J. W. B. & Watson, A. J. B., 31 May 2021, (E-pub ahead of print) Reference Module in Chemistry, Molecular Sciences and Chemical Engineering. Elsevier Inc.

    Research output: Chapter in Book/Report/Conference proceedingChapter

  2. Cu(OTf)2-mediated cross-coupling of nitriles and N-heterocycles with arylboronic acids to generate nitrilium and pyridinium products

    Bell, N., Xu, C., Fyfe, J., Vantourout, J. C., Brals, J., Chabbra, S., Bode, B. E., Cordes, D. B., Slawin, A. M. Z., McGuire, T. M. & Watson, A. J. B., 29 Mar 2021, In: Angewandte Chemie International Edition. 60, 14, p. 7935-7940 7 p.

    Research output: Contribution to journalArticlepeer-review

  3. In vivo half-life extension of BMP1/TLL metalloproteinase inhibitors using small-molecule human serum albumin binders

    Vantourout, J. C., Mason, A. M., Yuen, J., Simpson, G. L., Evindar, G., Kuai, L., Hobbs, M., Edgar, E., Needle, S., Bai, X., Wilson, S., Scott-Stevens, P., Traylen, W., Lambert, K., Young, N., Bunally, S., Summerfield, S. G., Snell, R., Lad, R., Shi, E. & 13 others, Skinner, S., Shewchuk, L., Watson, A. J. B., Chung, C-W., Pal, S., Holt, D. A., Kallander, L. S., Prendergast, J., Rivera, K., Washburn, D. G., Harpel, M. R., Arico-Muendel, C. & Isidro-Llobet, A., 17 Feb 2021, In: Bioconjugate Chemistry. 32, 2

    Research output: Contribution to journalArticlepeer-review

  4. First experimental evidence for a bis-ethene chromium(I) complex forming from an activated ethene oligomerization catalyst

    Chabbra, S., Smith, D. M., Bell, N. L., Watson, A. J. B., Buehl, M., Cole-Hamilton, D. J. & Bode, B. E., 18 Dec 2020, In: Science Advances. 6, 51, 7 p., eabd7057.

    Research output: Contribution to journalArticlepeer-review

  5. Catalytic enantioselective synthesis of heterocyclic vicinal fluoroamines using asymmetric protonation: a method development and mechanistic study

    Ashford, M., Xu, C., Molloy, J. J., Carpenter-Warren, C. L., Slawin, A. M. Z., Leach, A. G. & Watson, A. J. B., 21 Sep 2020, In: Chemistry - A European Journal. 26, 53, p. 12249-12255 8 p.

    Research output: Contribution to journalArticlepeer-review

Related by journal

  1. The problem with problems: fundamental to applied research using palladium

    Watson, A. J. B., 5 May 2020, (E-pub ahead of print) In: Synlett. 31

    Research output: Contribution to journalArticlepeer-review

  2. Isothiourea-catalysed sequential kinetic resolution of acyclic (±)-1,2-diols

    Harrer, S., Greenhalgh, M. D., Neyyappadath, R. M. & Smith, A. D., Aug 2019, In: Synlett. 30, 13, p. 1555-1560

    Research output: Contribution to journalArticlepeer-review

  3. A cascade Suzuki-Miyaura/Diels-Alder protocol: exploring the bifunctional utility of vinyl Bpin

    Cain, D. L., McLaughlin, C., Molloy, J., Carpenter-Warren, C., Anderson, N. A. & Watson, A. J. B., Apr 2019, In: Synlett. 30, 7, p. 787-791 5 p.

    Research output: Contribution to journalArticlepeer-review

  4. Application of one-pot three-component condensation reaction for the synthesis of new organophosphorus-sulfur macrocycles

    Hua, G., Cordes, D. B., Slawin, A. M. Z. & Woollins, J. D., 19 Apr 2018, (E-pub ahead of print) In: Synlett. eFirst

    Research output: Contribution to journalArticlepeer-review

ID: 255931977

Top