21403-36-1Relevant articles and documents
Synthesis of hydronaphthalenes through coupling of enyne-carbonyl compounds that contain pendant alkane groups with Fischer carbene complexes
Patti, Rajesh Kumar,Duan, Shaofeng,Camacho-Davila, Alejandro,Waynant, Kris,Dunn, Kenneth A.,Herndon, James W.
, p. 3682 - 3684 (2010)
The coupling of enyne-carbonyl compounds that contain pendant alkene groups with Fischer carbine complexes to afford furans that contain pendant alkene groups is described. Subsequent intramolecular DielsAlder reactions are effective in selected cases, resulting in hydronaphthalene systems after dehydration. Although the DielsAlder event is thermodynamically unfavorable, the overall transformation of alkenefurans to dihydronaphthalenes is a favorable process.
Photocatalytic Decarboxylative [3 + 2] and [4 + 2] Annulation of Enynals and γ,σ-Unsaturated N-(Acyloxy)phthalimides by NaI/PPh3Catalysis
Liu, Xiao-Jie,Zhou, Sheng-Yun,Xiao, Yuting,Sun, Qing,Lu, Xin,Li, Yang,Li, Jin-Heng
supporting information, p. 7839 - 7844 (2021/10/20)
A practical and eco-friendly strategy for the radical-mediated decarboxylative [3 + 2] and [4 + 2] annulation of enynals and γ,σ-unsaturated N-(acyloxy)phthalimides through the photoactivation of an electron donor-acceptor (EDA) complex has been developed. A wide range of primary, secondary, and tertiary alkyl N-hydroxyphthalimide (NHP) esters can be used as suitable substrates for the synthesis of fused ketones without any transition-metal catalysts or oxidants. This protocol features a broad substrate scope, excellent selectivity, and clean reaction conditions.
Palladium-catalyzed carbene migratory insertion using conjugated ene-yne-ketones as carbene precursors
Xia, Ying,Qu, Shuanglin,Xiao, Qing,Wang, Zhi-Xiang,Qu, Peiyuan,Chen, Li,Liu, Zhen,Tian, Leiming,Huang, Zhongxing,Zhang, Yan,Wang, Jianbo
supporting information, p. 13502 - 13511 (2013/09/24)
Palladium-catalyzed cross-coupling reactions between benzyl, aryl, or allyl bromides and conjugated ene-yne-ketones lead to the formation of 2-alkenyl-substituted furans. This novel coupling reaction involves oxidative addition, alkyne activation-cyclization, palladium carbene migratory insertion, β-hydride elimination, and catalyst regeneration. Palladium (2-furyl)carbene is proposed as the key intermediate, which is supported by DFT calculations. The palladium carbene character of the key intermediate is validated by three aspects, including bond lengths, Wiberg bond order indices, and molecular orbitals, by comparison to those reported for stable palladium carbene species. Computational studies also revealed that the rate-limiting step is ene-yne-ketone cyclization, which leads to the formation of the palladium (2-furyl)carbene, while the subsequent carbene migratory insertion is a facile process with a low energy barrier (5 kcal/mol).
THERMALLY INITIATED REACTIONS OF (Z)-EPOXYHEXENYNES A FACILE PREPARATION OF 3,4-ANNULATED FURANS
Eberbach, Wolfgang,Roser, Joachim
, p. 2221 - 2234 (2007/10/02)
An efficient and general access to 3,4-annulated 2-vinylfurans (type II) is provided by the thermally induced ring transformation of epoxyhexenynes (I).Depending on the substitution pattern the reactions proceed either by heating in solution (5a-h) or under short-time thermolysis conditions (6i, j).The results are consistent with a multistep mechanism involving 1-oxacyclohepta-3,4,6-trienes as central intermediates.
