Synthesis and catalytic properties of palladium(ii) complexes with P,π-chelating ferrocene phosphinoallyl ligands and their non-tethered analogues
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388980%3A_____%2F24%3A00585909" target="_blank" >RIV/61388980:_____/24:00585909 - isvavai.cz</a>
Alternative codes found
RIV/00216208:11310/24:10480929
Result on the web
<a href="https://hdl.handle.net/11104/0353760" target="_blank" >https://hdl.handle.net/11104/0353760</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/d4dt00961d" target="_blank" >10.1039/d4dt00961d</a>
Alternative languages
Result language
angličtina
Original language name
Synthesis and catalytic properties of palladium(ii) complexes with P,π-chelating ferrocene phosphinoallyl ligands and their non-tethered analogues
Original language description
Hybrid phosphines usually combine a phosphine moiety with another heteroatom secondary donor group in their structures while compounds equipped with hydrocarbyl pi-donor moieties remain uncommon. This contribution reports the synthesis and structural characterization of the first P/pi-allyl-chelating complexes that were obtained using the structurally flexible and redox-active ferrocene unit as the scaffold, viz. [PdCl(R(2)PfcCHCHCH(2)-eta(3):kappa P)] (1 (R), R = Ph and cyclohexyl (Cy), fc = ferrocene-1,1 '-diyl). These compounds were synthesized from the respective phosphinoferrocene carboxaldehydes R(2)PfcCHO via reaction with vinylmagnesium bromide to generate 1-(phosphinoferrocenyl)allyl alcohols, which were subsequently acetylated. The resulting allyl acetates reacted smoothly with [Pd-2(dba)(3)]/[Et3NH]Cl (dba = dibenzylideneacetone) to produce the target compounds. Complexes 1 (R) and their nontethered analogues [PdCl(eta(3)-C3H5)(FcPR(2)-kappa P)] (5 (R), Fc = ferrocenyl) were evaluated as pre-catalysts for the Pd-catalysed allylic amination of cinnamyl acetate with aliphatic amines and Suzuki-Miyaura-type cross-coupling of 4-tolylboronic acid with benzoyl chloride. In these reactions, better results were achieved with compounds 5 (R) (particularly with 5(Ph)), presumably because they form more stable LPd(0)-type catalysts.
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
—
OECD FORD branch
10402 - Inorganic and nuclear chemistry
Result continuities
Project
<a href="/en/project/GA23-06718S" target="_blank" >GA23-06718S: Rigid and functional ferrocene phosphines</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2024
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Dalton Transactions
ISSN
1477-9226
e-ISSN
1477-9234
Volume of the periodical
53
Issue of the periodical within the volume
20
Country of publishing house
GB - UNITED KINGDOM
Number of pages
10
Pages from-to
8722-8731
UT code for WoS article
001214915000001
EID of the result in the Scopus database
2-s2.0-85192481570