FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2952694920> ?p ?o ?g. }

• W2952694920 endingPage "4062" @default.
• W2952694920 startingPage "4053" @default.
• W2952694920 abstract "An efficient method for the synthesis of 1,7-enyne derivatives via phosphine−palladium-catalyzed three-component assembling of activated olefins, allylic chlorides, and allenylstannanes is described. Substituted arylethylidene malononitriles 1a−g (RCHC(CN)2: R = C6H5 (1a), p-ClC6H4 (1b), p-OMeC6H4 (1c), p-NO2C6H4 (1d), 1-naphthyl (1e), 2-furyl (1f), and 2-thienyl (1g)) undergo propargylallylation with allylic chlorides 2a−e (allyl chloride (2a), methallyl chloride (2b), 4-chloropent-2-ene (2c), cinnamyl chloride (2d), and 3-chlorocyclohexene (2e)) and n-tributylallenylstannane (n-Bu3SnCHCCH2, 3a) in the presence of Pd(PPh3)4 in toluene to afford the corresponding 1,7-enyne derivatives 4a−m in good to excellent yields. The catalytic reaction is highly regioselective, with the propargyl group adding to the carbon where the R group is attached and the allyl group adding to the carbon connected to the CN groups of activated olefins 1a−g. The present catalytic reaction is successfully extended to substituted arylethylidene-1,3-indanediones 5a−j (RCH = (1,3-indanedione): R = C6H5 (5a), p-ClC6H4 (5b), p-BrC6H4 (5c), p-OMeC6H4 (5d), p-NO2C6H4 (5e), p-CNC6H4 (5f), p-biphenyl (5g), 1-naphthyl (5h), 2-thienyl (5i), and 2-benzo[b]furane-2-yl (5j)) and substituted 2,2-dimethyl-5-(arylethylidene)-1,3-dioxane-4,6-diones 7a,b (RCH = (1,3-dioxane-4,6-dione): R = p-NO2C6H4 (7a), p-OMeC6H4 (7b)). The three-component assembling of these substrates with allylic chlorides (2a,b,d,e) and n-tributylallenylstannane (n-Bu3SnCHCCH2, 3a) proceeds smoothly to afford the corresponding 1,7-enyne derivatives 6a−m and 8a−d in good to excellent yields. The catalytic propargylallylation can be further applied to the activated dienes, C6H5CHCHCR2 (R2 = (CN)2 (9a), 1,3-indanedione (9b), 2,2-dimethyl-1,3-dioxane-4,6-dione (9c)), with allylic chlorides (2a,b,d) and allenylstannane 3a to give regio- and chemoselective 1,2-addition products 10a−h in good to excellent yields. A plausible mechanism based on an η1-allenyl η3-allyl palladium intermediate is proposed to account for the catalytic three-component reaction." @default.
• W2952694920 created "2019-06-27" @default.
• W2952694920 creator A5039710142 @default.
• W2952694920 creator A5048288704 @default.
• W2952694920 creator A5069900066 @default.
• W2952694920 date "2004-05-11" @default.
• W2952694920 modified "2023-09-24" @default.
• W2952694920 title "Highly Regio- and Chemoselective Palladium-Catalyzed Propargylallylation of Activated Olefins: A Novel Route to 1,7-Enyne Derivatives" @default.
• W2952694920 cites W1972564520 @default.
• W2952694920 cites W1981442284 @default.
• W2952694920 cites W1981987358 @default.
• W2952694920 cites W1986869195 @default.
• W2952694920 cites W1990929089 @default.
• W2952694920 cites W1997159586 @default.
• W2952694920 cites W1999081018 @default.
• W2952694920 cites W2002388060 @default.
• W2952694920 cites W2003194091 @default.
• W2952694920 cites W2003504152 @default.
• W2952694920 cites W2009322826 @default.
• W2952694920 cites W2031050639 @default.
• W2952694920 cites W2031966729 @default.
• W2952694920 cites W2033324096 @default.
• W2952694920 cites W2036539800 @default.
• W2952694920 cites W2046809968 @default.
• W2952694920 cites W2059324925 @default.
• W2952694920 cites W2080949352 @default.
• W2952694920 cites W2084359687 @default.
• W2952694920 cites W2088275455 @default.
• W2952694920 cites W2089125473 @default.
• W2952694920 cites W2094810376 @default.
• W2952694920 cites W2098220966 @default.
• W2952694920 cites W2123295946 @default.
• W2952694920 cites W2127603052 @default.
• W2952694920 cites W2146451905 @default.
• W2952694920 cites W2171224377 @default.
• W2952694920 cites W2172533469 @default.
• W2952694920 cites W2176871217 @default.
• W2952694920 cites W2477643812 @default.
• W2952694920 cites W2949136223 @default.
• W2952694920 cites W2949252648 @default.
• W2952694920 cites W2950041683 @default.
• W2952694920 cites W2950149042 @default.
• W2952694920 cites W2950177721 @default.
• W2952694920 cites W2950207551 @default.
• W2952694920 cites W2950638031 @default.
• W2952694920 cites W2950645915 @default.
• W2952694920 cites W2950707828 @default.
• W2952694920 cites W2950786941 @default.
• W2952694920 cites W2951317440 @default.
• W2952694920 cites W2951397253 @default.
• W2952694920 cites W2951674713 @default.
• W2952694920 cites W2951957837 @default.
• W2952694920 cites W2952347423 @default.
• W2952694920 cites W2952414062 @default.
• W2952694920 cites W2952728674 @default.
• W2952694920 cites W2953163093 @default.
• W2952694920 cites W3004477108 @default.
• W2952694920 doi "https://doi.org/10.1021/jo0496998" @default.
• W2952694920 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/15176830" @default.
• W2952694920 hasPublicationYear "2004" @default.
• W2952694920 type Work @default.
• W2952694920 sameAs 2952694920 @default.
• W2952694920 citedByCount "26" @default.
• W2952694920 countsByYear W29526949202012 @default.
• W2952694920 countsByYear W29526949202013 @default.
• W2952694920 countsByYear W29526949202017 @default.
• W2952694920 countsByYear W29526949202018 @default.
• W2952694920 countsByYear W29526949202019 @default.
• W2952694920 countsByYear W29526949202020 @default.
• W2952694920 crossrefType "journal-article" @default.
• W2952694920 hasAuthorship W2952694920A5039710142 @default.
• W2952694920 hasAuthorship W2952694920A5048288704 @default.
• W2952694920 hasAuthorship W2952694920A5069900066 @default.
• W2952694920 hasConcept C120095180 @default.
• W2952694920 hasConcept C155647269 @default.
• W2952694920 hasConcept C161790260 @default.
• W2952694920 hasConcept C178790620 @default.
• W2952694920 hasConcept C185592680 @default.
• W2952694920 hasConcept C2777716191 @default.
• W2952694920 hasConcept C2778695967 @default.
• W2952694920 hasConcept C2780437523 @default.
• W2952694920 hasConcept C2780588603 @default.
• W2952694920 hasConcept C502130503 @default.
• W2952694920 hasConcept C59759590 @default.
• W2952694920 hasConcept C71240020 @default.
• W2952694920 hasConceptScore W2952694920C120095180 @default.
• W2952694920 hasConceptScore W2952694920C155647269 @default.
• W2952694920 hasConceptScore W2952694920C161790260 @default.
• W2952694920 hasConceptScore W2952694920C178790620 @default.
• W2952694920 hasConceptScore W2952694920C185592680 @default.
• W2952694920 hasConceptScore W2952694920C2777716191 @default.
• W2952694920 hasConceptScore W2952694920C2778695967 @default.
• W2952694920 hasConceptScore W2952694920C2780437523 @default.
• W2952694920 hasConceptScore W2952694920C2780588603 @default.
• W2952694920 hasConceptScore W2952694920C502130503 @default.
• W2952694920 hasConceptScore W2952694920C59759590 @default.
• W2952694920 hasConceptScore W2952694920C71240020 @default.
• W2952694920 hasIssue "12" @default.

• next