English (United Kingdom)

https://curated-unify.zendy.io/wp-json/zendy-region/v1/featured_content/oa?rat=en

https://curated-unify.zendy.io/wp-json/zendy-region/v1/highlighted_journal/

Global: Zendy Plus annual

Presents the access of premium content as premium feature

Premium Content

Presents the keyphrase highlighting as premium feature

Keyphrase Highlighting

Presents the summarisation as premium feature

Summarisation

Insights

Presents the pdf analysis as premium feature

PDF Analysis

Presents the zaia usage as premium feature

ZAIA

Global: Zendy Tools annual

Global: Zendy Free Plan

Global: Zendy Tools monthly

Global: Zendy Plus monthly

Significance: Reported is the synthesis of 5-arylfuranones by the three-component reaction of aryl halides, carbon monoxide, and alkenes in the presence of PdBr2, cataCXium POMeCy as ligand L and triethylamine as base. In the exploration of the scope of the reaction, substituted aryl bromides, aryl iodides, and different alkenes were tested. Aryl bromides bearing electron-donating groups (R1 = t-Bu, 3-OMe, 4-OMe) led to furanones in 55–77% yield. However, aryl and alkyl bromides with electron-withdrawing groups, such as 4-bromoacetophenone, 4-bromoacetaldehyde and 4-bromobenzonitrile produced only trace amounts of products. Some bromo heterocycles including bromothiophene, bromobenzothiophene, benzodioxole, and indole derivatives were also tolerated. Terminal alkenes with R2 = n-Bu, Cy, TES afforded furanones in 54–73% yield, while an alkene with R2 = CH2CH2Ph form the desired product in only 28% yield with a greater amount of the isomeric 3-alkyl-5-aryl-substituted furanone being formed. Comment: Synthetic furanone compounds have been shown to inhibit bacterial quorum sensing in P. aeruginosa and to exhibit favorable therapeutic effects on P. aeruginosa lung infection (H. Wu et al. J. Antimicrob. Chemother. 2004, 53, 1054). In the present double carbonylative Heck reaction, optimization of the reaction using different ligands, solvents, and the effect of carbon monoxide pressure was explored; increasing the carbon monoxide pressure from 5 to 20 bar resulted in improved yield. Use of inorganic base in the reaction failed to give furanone products. Similar reactivity was observed when aryl iodides were employed in place of aryl bromides. 23 examples 28–87% yield PdBr2 (5 mol%) L (10 mol%) X

Synthesis of 5-Arylfuranones via a Carbonylative Heck Reaction