Skip to content

Research at St Andrews

Ni vs. Pd in Suzuki-Miyaura sp2-sp2 cross-coupling: a head-to-head study in a comparable precatalyst/ligand system

Research output: Contribution to journalArticle

DOI

Open Access Status

  • Embargoed (until 29/04/20)

Abstract

The Suzuki-Miyaura reaction is a cornerstone method for sp2-sp2 cross-coupling in industry. There has been a concerted effort to enable the use of Ni catalysis as an alternative to Pd in order to mitigate cost and improve sustainability. Despite significant advances, ligand development for Ni-catalyzed Suzuki-Miyaura cross-coupling remains underdeveloped when compared to Pd and, as a consequence, ligands for Ni-catalyzed processes are typically taken from the Pd arena. In this study we evaluate the effect of using a similar Ni and Pd precatalyst based on a common bidentate ligand (dppf) in a head-to-head format for the most common type of biaryl couplings, establishing the practical implications of direct replacement of Pd with Ni, and identifying the potential origins of these observations in a mechanistic context.
Close

Details

Original languageEnglish
Pages (from-to)5055-5059
JournalOrganic & Biomolecular Chemistry
Volume17
Issue number20
Early online date29 Apr 2019
DOIs
Publication statusPublished - 28 May 2019

Discover related content
Find related publications, people, projects and more using interactive charts.

View graph of relations

Related by author

  1. Mechanistic development and recent applications of the Chan–Lam amination

    West, M., Fyfe, J., Vantourout, J. C. & Watson, A. J. B., 22 Nov 2019, In : Chemical Reviews. Articles ASAP

    Research output: Contribution to journalReview article

  2. Discovery, scope, and limitations of an N-dealkylation/N-arylation of secondary sulfonamides under Chan–Lam conditions

    West, M., Thomson, B., Vantourout, J. C. & Watson, A. J. B., 18 Nov 2019, In : Asian Journal of Organic Chemistry. Early View

    Research output: Contribution to journalArticle

  3. Mechanism of Cu-catalyzed aryl boronic acid halode-boronation using electrophilic halogen: development of a base-catalyzed Iododeboronation for radiolabeling applications

    Molloy, J., O’Rourke, K., Frias, C., Sloan, N., West, M., Pimlott, S., Sutherland, A. & Watson, A. J. B., 5 Apr 2019, In : Organic Letters. 21, 7, p. 2488-2492 5 p.

    Research output: Contribution to journalArticle

  4. 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 journalArticle

  5. N-Alkyl-α-amino acids in Nature and their biocatalytic preparation

    Hyslop, J. F., Lovelock, S. L., Watson, A. J. B., Sutton, P. W. & Roiban, G-D., 10 Mar 2019, In : Journal of Biotechnology. 293, p. 56-65 10 p.

    Research output: Contribution to journalArticle

Related by journal

  1. Organic & Biomolecular Chemistry (Journal)

    Stuart John Conway (Editor)
    2007 → …

    Activity: Publication peer-review and editorial work typesEditor of research journal

Related by journal

  1. Probing the helical integrity of multivicinal all-syn-fluoro alkanes

    Al-Maharik, N., Cordes, D. B., Slawin, A. M. Z., Buhl, M. & O'Hagan, D., 7 Feb 2020, In : Organic & Biomolecular Chemistry. 18, 5, p. 878-887 10 p.

    Research output: Contribution to journalArticle

  2. An enzymatic Finkelstein reaction: fluorinase catalyses direct halogen exchange

    Lowe, P. T., Cobb, S. L. & O'Hagan, D., 28 Aug 2019, In : Organic & Biomolecular Chemistry. 17, 32, p. 7493-7496 4 p.

    Research output: Contribution to journalArticle

  3. Enzymatic radiosynthesis of a 18F-Glu-Ureido-Lys ligand for the prostate-specific membrane antigen (PSMA)

    Lowe, P. T., Dall'Angelo, S., Fleming, I. N., Piras, M., Zanda, M. & O'Hagan, D., 14 Feb 2019, In : Organic & Biomolecular Chemistry. 17, 6, p. 1480-1486 7 p.

    Research output: Contribution to journalArticle

  4. Evaluating aryl esters as bench-stable C(1)-ammonium enolate precursors in catalytic, enantioselective Michael addition-lactonisations

    Young, C. M., Taylor, J. E. & Smith, A. D., 21 May 2019, In : Organic & Biomolecular Chemistry. 17, 19, p. 4747-4752

    Research output: Contribution to journalArticle

ID: 258978911

Top