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

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GA23-05752S" target="_blank" >GA23-05752S: Chytrá léčiva: Nové conjugovatelné self-immolativní spojky pro cílené doručení léčiv</a><br>

Návaznosti

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

Rok uplatnění

2023

Kód důvěrnosti údajů

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

Název periodika

Green Chemistry

ISSN

1463-9262

e-ISSN

1463-9270

Svazek periodika

25

Číslo periodika v rámci svazku

23

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

16

Strana od-do

9779-9794

Kód UT WoS článku

001094117700001

EID výsledku v databázi Scopus

2-s2.0-85175572622