Matches in SemOpenAlex for { <https://semopenalex.org/work/W2070424539> ?p ?o ?g. }
- W2070424539 endingPage "5344" @default.
- W2070424539 startingPage "5338" @default.
- W2070424539 abstract "Abstract The palladium‐catalyzed tandem reactions of yne–propargylic carbonates with aryl boronic acids, 2‐furyl boronic acid, and 2‐thiopheneboronic acid, followed by 6π‐electrocyclization to give fused ring aromatic products such as naphthalene, benzofuran, and benzothiophene derivatives are realized. Screening of the reaction conditions revealed that the combination of [Pd(PPh 3 ) 4 ] in THF gave the best results in terms of reactivity and product yields in the reaction of yne–propargylic carbonates with phenylboronic acid. The reaction is sensitive toward steric hindrance when substituted phenylboronic acids are emplyed. However, when we take 2‐furyl boronic acid as the organometallic reagent, most substrates perform very well to give benzofuran derivatives. In addition, 2‐thiopheneboronic acid is also a very effective coupling reagent to give bezothiophenes in high yields. A mechanism is proposed that involves the formation of an allenylpalladium complex from Pd 0 and propargylic carbonate, followed by insertion of an intramolecular triple bond and the Suzuki coupling reaction, and then electrocyclization." @default.
- W2070424539 created "2016-06-24" @default.
- W2070424539 creator A5001416622 @default.
- W2070424539 creator A5005997337 @default.
- W2070424539 creator A5054631829 @default.
- W2070424539 creator A5063288717 @default.
- W2070424539 date "2004-10-20" @default.
- W2070424539 modified "2023-10-16" @default.
- W2070424539 title "Palladium-Catalyzed Tandem Reaction of Yne-Propargylic Carbonates with Boronic Acids: A Simple Method for the Synthesis of Fused Aromatic Rings through Allene-Mediated Electrocyclization" @default.
- W2070424539 cites W1038509922 @default.
- W2070424539 cites W1966591284 @default.
- W2070424539 cites W1971121155 @default.
- W2070424539 cites W1980734460 @default.
- W2070424539 cites W1992383305 @default.
- W2070424539 cites W1997816697 @default.
- W2070424539 cites W2007453313 @default.
- W2070424539 cites W2010928838 @default.
- W2070424539 cites W2024347323 @default.
- W2070424539 cites W2026435779 @default.
- W2070424539 cites W2029136697 @default.
- W2070424539 cites W2033212555 @default.
- W2070424539 cites W2043629906 @default.
- W2070424539 cites W2051112727 @default.
- W2070424539 cites W2051434700 @default.
- W2070424539 cites W2053473549 @default.
- W2070424539 cites W2069054853 @default.
- W2070424539 cites W2073101910 @default.
- W2070424539 cites W2073321812 @default.
- W2070424539 cites W2073480964 @default.
- W2070424539 cites W2085902135 @default.
- W2070424539 cites W2134199244 @default.
- W2070424539 cites W2149043386 @default.
- W2070424539 cites W2337695151 @default.
- W2070424539 cites W2949644941 @default.
- W2070424539 cites W2950473000 @default.
- W2070424539 cites W2951121884 @default.
- W2070424539 cites W2951185666 @default.
- W2070424539 cites W2951456834 @default.
- W2070424539 cites W2951588054 @default.
- W2070424539 cites W2951715500 @default.
- W2070424539 cites W2952287638 @default.
- W2070424539 cites W2952460025 @default.
- W2070424539 cites W2952967697 @default.
- W2070424539 cites W3004575003 @default.
- W2070424539 cites W4236524239 @default.
- W2070424539 doi "https://doi.org/10.1002/chem.200400573" @default.
- W2070424539 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/15378726" @default.
- W2070424539 hasPublicationYear "2004" @default.
- W2070424539 type Work @default.
- W2070424539 sameAs 2070424539 @default.
- W2070424539 citedByCount "36" @default.
- W2070424539 countsByYear W20704245392012 @default.
- W2070424539 countsByYear W20704245392013 @default.
- W2070424539 countsByYear W20704245392014 @default.
- W2070424539 countsByYear W20704245392015 @default.
- W2070424539 countsByYear W20704245392016 @default.
- W2070424539 countsByYear W20704245392017 @default.
- W2070424539 countsByYear W20704245392018 @default.
- W2070424539 countsByYear W20704245392019 @default.
- W2070424539 countsByYear W20704245392021 @default.
- W2070424539 countsByYear W20704245392022 @default.
- W2070424539 crossrefType "journal-article" @default.
- W2070424539 hasAuthorship W2070424539A5001416622 @default.
- W2070424539 hasAuthorship W2070424539A5005997337 @default.
- W2070424539 hasAuthorship W2070424539A5054631829 @default.
- W2070424539 hasAuthorship W2070424539A5063288717 @default.
- W2070424539 hasConcept C13205572 @default.
- W2070424539 hasConcept C155647269 @default.
- W2070424539 hasConcept C161790260 @default.
- W2070424539 hasConcept C178790620 @default.
- W2070424539 hasConcept C185592680 @default.
- W2070424539 hasConcept C21951064 @default.
- W2070424539 hasConcept C2776589655 @default.
- W2070424539 hasConcept C2777734296 @default.
- W2070424539 hasConcept C2777864310 @default.
- W2070424539 hasConcept C2778652500 @default.
- W2070424539 hasConcept C2780263894 @default.
- W2070424539 hasConcept C2781076698 @default.
- W2070424539 hasConcept C40875361 @default.
- W2070424539 hasConcept C48424934 @default.
- W2070424539 hasConcept C502130503 @default.
- W2070424539 hasConcept C75079739 @default.
- W2070424539 hasConceptScore W2070424539C13205572 @default.
- W2070424539 hasConceptScore W2070424539C155647269 @default.
- W2070424539 hasConceptScore W2070424539C161790260 @default.
- W2070424539 hasConceptScore W2070424539C178790620 @default.
- W2070424539 hasConceptScore W2070424539C185592680 @default.
- W2070424539 hasConceptScore W2070424539C21951064 @default.
- W2070424539 hasConceptScore W2070424539C2776589655 @default.
- W2070424539 hasConceptScore W2070424539C2777734296 @default.
- W2070424539 hasConceptScore W2070424539C2777864310 @default.
- W2070424539 hasConceptScore W2070424539C2778652500 @default.
- W2070424539 hasConceptScore W2070424539C2780263894 @default.
- W2070424539 hasConceptScore W2070424539C2781076698 @default.
- W2070424539 hasConceptScore W2070424539C40875361 @default.
- W2070424539 hasConceptScore W2070424539C48424934 @default.
- W2070424539 hasConceptScore W2070424539C502130503 @default.
- W2070424539 hasConceptScore W2070424539C75079739 @default.