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Surfactant Technology: With New Rules, Designing New Sequences Is Required!

  • Daniel J. Lippincott
    Daniel J. Lippincott
    Department of Chemistry & Biochemistry, University of California, Santa Barbara, California 93106, United States
  • Evan Landstrom
    Evan Landstrom
    Department of Chemistry & Biochemistry, University of California, Santa Barbara, California 93106, United States
  • Margery Cortes-Clerget
    Margery Cortes-Clerget
    Chemical & Analytical Development, Novartis Pharma AG, 4056 Basel, Switzerland
  • Bruce H. Lipshutz
    Bruce H. Lipshutz
    Department of Chemistry & Biochemistry, University of California, Santa Barbara, California 93106, United States
  • Klaus Buescher
    Klaus Buescher
    Chemical & Analytical Development, Novartis Pharma AG, 4056 Basel, Switzerland
  • Robert Schreiber
    Robert Schreiber
    Chemical & Analytical Development, Novartis Pharma AG, 4056 Basel, Switzerland
  • Corinne Durano
    Corinne Durano
    Chemical & Analytical Development, Novartis Pharma AG, 4056 Basel, Switzerland
  • Michael Parmentier
    Michael Parmentier
    Chemical & Analytical Development, Novartis Pharma AG, 4056 Basel, Switzerland
  • Ning Ye
    Ning Ye
    Chemical & Analytical Development, Suzhou Novartis Pharma Technology Company Limited, Changshu, Jiangsu 215537, China
    More by Ning Ye
  • Bin Wu
    Bin Wu
    Chemical & Analytical Development, Suzhou Novartis Pharma Technology Company Limited, Changshu, Jiangsu 215537, China
    More by Bin Wu
  • Min Shi
    Min Shi
    Chemical & Analytical Development, Suzhou Novartis Pharma Technology Company Limited, Changshu, Jiangsu 215537, China
    More by Min Shi
  • Hongwei Yang
    Hongwei Yang
    Chemical & Analytical Development, Suzhou Novartis Pharma Technology Company Limited, Changshu, Jiangsu 215537, China
    More by Hongwei Yang
  • Martin Andersson
    Martin Andersson
    Department of Chemical and Biochemical Engineering, Technical University of Denmark, DK-2800 Kongens Lyngby, Denmark
  • , and 
  • Fabrice Gallou*
    Fabrice Gallou
    Chemical & Analytical Development, Novartis Pharma AG, 4056 Basel, Switzerland
    *E-mail: [email protected]
Cite this: Org. Process Res. Dev. 2020, 24, 5, 841–849
Publication Date (Web):December 2, 2019
https://doi.org/10.1021/acs.oprd.9b00454
Copyright © 2019 American Chemical Society

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    Abstract

    Abstract Image

    With a growing toolbox of surfactant-mediated chemistry in water and an increased number of scaled-up transformations has come tremendous learning [for example, see: Lipshutz, B. H.; et al. The Hydrophobic Effect Applied to Organic Synthesis: Recent Synthetic Chemistry “in Water”. Chem. - Eur. J. 2018, 24 (26), 6672–6695]. These opportunities now reside within a few expert groups, and while all of the details are far from fully understood or still under development, substantial know-how has been gained in both reaction process and synthesis design. Herein we share some of the fundamental principles inherent to micellar catalysis and illustrate them on a particularly challenging case involving a Suzuki–Miyaura cross-coupling. The complete structures of the active pharmaceutical ingredient (API) and the intermediates are not fully disclosed for confidentiality reasons but can nevertheless serve as illustrative of the importance of factors that, unlike traditional chemistry in organic solvents, can be crucial to a successful outcome (e.g., lipophilicity). The API used as an example for this discussion bears significant commonality with a large number of other targets associated with the formation of a biphenyl array as well as the presence of an amide and products resulting from nucleophilic aromatic substitutions (SNAr). Hence, we look to utilize these prior learnings and can now rapidly apply them to the design of optimal conditions for several other important transformations.

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    Cited By

    This article is cited by 48 publications.

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