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Ligand-free palladium-catalyzed tandem pathways for the synthesis of 4,4-diarylbutanones and 4,4-diaryl-3-butenones under microwave conditions.
Autorzy
Rok wydania
2019
Czasopismo
Applied Organometallic Chemistry
Numer woluminu
33
Strony
e4870/1-e4870/9
DOI
10.1002/aoc.4870
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
Two efficient Pd‐catalyzed tandem pathways for the synthesis of 4,4‐diaryl‐2‐butanones and 4,4‐diaryl‐3‐buten‐2‐ones were elaborated. The first step in both procedures was the Heck coupling of methyl vinyl ketone (MVK) and various aryl iodides leading to 4‐aryl‐3‐buten‐2‐one with the yield of up to 92% in 1 hr. The second step performed with the same catalyst and a new portion of aryl iodide in the presence K2CO3 as a base produced 4,4‐diaryl‐3‐buten‐2‐ones in high yield. Reaction selectivity changed completely to saturated 4,4‐diaryl‐2‐butanones, reductive Heck products, when a tertiary amine was used instead of K2CO3. Due to the application of microwave irradiation (MW), the desired products were obtained in high yield in a short time (4 hr), using 0.5 mol% of the Pd (OAc)2 catalyst without additional ligands.
Słowa kluczowe
diaryl‐ketones, Heck coupling, MW irradiation, palladium, reductive Heck coupling
Adres publiczny
http://dx.doi.org/10.1002/aoc.4870
Strona internetowa wydawcy
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