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Multimetallic Pd- and Ni-catalyzed C(sp2)-P cross-coupling under aqueous micellar conditions

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F23%3A10474363" target="_blank" >RIV/00216208:11310/23:10474363 - isvavai.cz</a>

  • Result on the web

    <a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=2mjPjR_lo9" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=2mjPjR_lo9</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1039/d3gc02735j" target="_blank" >10.1039/d3gc02735j</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Multimetallic Pd- and Ni-catalyzed C(sp2)-P cross-coupling under aqueous micellar conditions

  • Original language description

    Organophosphorus compounds containing hydrolytically and metabolically stable C(sp(3))- and C(sp(2))-P bonds are widely used as reagents, ligands, pesticides, herbicides, flame retardants, surface modifiers, and antiviral and anticancer drugs. These applications rely on efficient C(sp(3))- and C(sp(2))-P bond-forming reactions. However, currently available C(sp(2))-P cross-coupling protocols require high catalyst loadings and temperatures, as well as environmentally unsustainable and harmful organic solvents (e.g., N,N-dimethylformamide, DMF). Herein, we disclose a conceptually novel strategy for performing multimetallic Pd/Ni- and dual-ligand Pd-catalyzed C(sp(2))-P cross-coupling reactions in aqueous micelles under mild and environmentally friendly conditions. Micellar catalysis in water enables C(sp(2))-P cross-coupling while avoiding environmentally unsustainable organic solvents, thereby reducing organic waste generation. Such micellar C(sp(2))-P cross-coupling reactions tolerate various functional groups and provide access to structurally diverse (hetero)aryl (thio)phosphonates, phosphinates and phosphine oxides using inexpensive commercial materials and catalysts. Moreover, C(sp(2))-P cross-coupling reactions of medically relevant substrates and drugs under late-stage functionalization settings and multistep one-pot processes highlight the potential applications of this experimental paradigm.

  • Czech name

  • Czech description

Classification

  • Type

    J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database

  • CEP classification

  • OECD FORD branch

    10401 - Organic chemistry

Result continuities

  • Project

    <a href="/en/project/GA23-05752S" target="_blank" >GA23-05752S: Making drugs smarter: Novel conjugable phosphorus-based linkers for targeted drug delivery</a><br>

  • Continuities

    P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Others

  • Publication year

    2023

  • Confidentiality

    S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Data specific for result type

  • Name of the periodical

    Green Chemistry

  • ISSN

    1463-9262

  • e-ISSN

    1463-9270

  • Volume of the periodical

    25

  • Issue of the periodical within the volume

    23

  • Country of publishing house

    GB - UNITED KINGDOM

  • Number of pages

    16

  • Pages from-to

    9779-9794

  • UT code for WoS article

    001094117700001

  • EID of the result in the Scopus database

    2-s2.0-85175572622