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
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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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