14920-89-9Relevant articles and documents
A new and efficient synthesis of rosefuran. A general synthesis of furans by palladium-catalysed cycloisomerization of (Z)-2-en-4-yn-1-ols
Gabriele, Bartolo,Salerno, Giuseppe
, p. 1083 - 1084 (1997)
(Z)-3,7-Dimethylocta-2,6-dien-4-yn-1-ol, readily available from (Z)-3-methylpent-2-en-4-yn-1-ol, undergoes cycloisomerization in the presence of catalytic amounts of K2PdI4 to give rosefuran in high yield.
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Chernysh et al.
, (1974)
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Palladium-catalyzed cycloisomerization of (Z)-enynols into furans using green solvents: Glycerol vs. water
Francos, Javier,Cadierno, Victorio
, p. 1552 - 1555 (2010)
Heteroannulation reactions of (Z)-2-en-4-yn-1-ol derivatives into furans can be conveniently performed in water and glycerol using cis-[PdCl 2(DAPTA)2] as catalyst. Higher activities were observed in an aqueous medium, but catalyst r
Benzimidazole, benzothiazole and benzoxazole ruthenium(II) complexes; catalytic synthesis of 2,3-dimethylfuran
Cetinkaya, Bekir,Oezdemir, Ismail,Bruneau, Christian,Dixneuf, Pierre H.
, p. 29 - 32 (2000)
Fourteen ruthenium(II) complexes of the type [RuCl2(η6-arene)L], (arene = 1,4-MeC6H4Pr(i) or C6Me6; L = benzimidazole derivative in which the NH group is substituted by N-alkyl or isoelectronic O or S atoms) have been prepared by cleavage of [RuCl2(η6-arene)]2 with the N-heterocycle L. Their spectroscopic and electrochemical properties are described. The effect of the nature of the benzazole (L) on the catalytic activity of these complexes for the intramolecular cyclization of (Z)-3-methylpent-2-en-4-yn-1- ol into 2,3-dimethylfuran has also been studied; the benzimidazole complexes were found to be the most active.
CYCLOADDITION REACTIONS OF POLYSUBSTITUTED FURANS WITH OXYALLYL CARBOCATIONS
Mann, John,Holland, Helen J.,Lewis, Terrence
, p. 2533 - 2542 (1987)
New and improved routes to polysubstituted furans are described, together with a survey of their reactivity in cycloaddition reactions with oxyallyl carbocations, producing polysubstituted 8-oxabicyclooct-6-3-ones.
Synthesis, Reactivity, and Coordination of Semihomologous dppf Congeners Bearing Primary Phosphine and Primary Phosphine Oxide Groups
Horky, Filip,Císa?ová, Ivana,?těpni?ka, Petr
, p. 427 - 441 (2021/02/06)
This contribution reports the synthesis of two phosphinoferrocene ligands desymmetrized by an inserted methylene spacer, viz., a bis-phosphine combining primary and tertiary phosphine moieties in its structure, Ph2PfcCH2PH2 (2), and a structurally unique, stable phosphine-primary phosphine oxide Ph2PfcCH2P(O)H2 (7; fc = ferrocene-1,1′-diyl). Compounds 2 and 7, together with 1,1′-bis(diphenylphosphino)ferrocene (dppf), the bis-tertiary phosphine Ph2PfcCH2PPh2, and the adduct Ph2P(BH3)fcCH2PH2 (6), were studied as ligands in Ru(II) complexes bearing auxiliary ν6-arene ligands and both free ligands and the isolated complexes were structurally authenticated, using spectroscopic methods and X-ray crystallography, and further investigated by cyclic voltammetry. The results suggest that distinct donor moieties in the unsymmetric ligands differentiate the otherwise identical coordinated metal centers and that the phosphine moiety in phosphine-phosphine oxide ligand 7 is preferably coordinated to Ru(II), before the phosphine oxide group, which must tautomerize into the hydroxyphosphine form prior to coordination.
S-Block cooperative catalysis: Alkali metal magnesiate-catalysed cyclisation of alkynols
Fairley, Michael,Davin, Laia,Hernán-Gómez, Alberto,García-álvarez, Joaquín,O'Hara, Charles T.,Hevia, Eva
, p. 5821 - 5831 (2019/06/18)
Mixed s-block metal organometallic reagents have been successfully utilised in the catalytic intramolecular hydroalkoxylation of alkynols. This success has been attributed to the unique manner in which these reagents can overcome the challenges of the reaction: namely OH activation and coordination to and then addition across a CC bond. In order to optimise the reaction conditions and to garner vital catalytic system requirements, a series of alkali metal magnesiates were enlisted for the catalytic intramolecular hydroalkoxylation of 4-pentynol. In a prelude to the main investigation, the homometallic magnesium dialkyl reagent MgR2 (where R = CH2SiMe3) was utilised. This reagent was unsuccessful in cyclising the alcohol into 2-methylenetetrahydrofuran 2a or 5-methyl-2,3-dihydrofuran 2b, even in the presence of multidentate Lewis donor molecules such as N,N,N′,N′′,N′′-pentamethyldiethylenetriamine (PMDETA). Alkali metal magnesiates MIMgR3 (when MI = Li, Na or K) performed the cyclisation unsatisfactorily both in the absence/presence of N,N,N′,N′-tetramethylethylenediamine (TMEDA) or PMDETA. When higher-order magnesiates (i.e., MI2MgR4) were employed, in general a marked increase in yield was observed for MI = Na or K; however, the reactions were still sluggish with long reaction times (22-36 h). A major improvement in the catalytic activity of the magnesiates was observed when the crown ether molecule 15-crown-5 was combined with sodium magnesiate Na2MgR4(TMEDA)2 furnishing yields of 87% with 2a:2b ratios of 95:5 after 5 h. Similar high yields of 88% with 2a:2b ratios of 90:10 after 3 h were obtained combining 18-crown-6 with potassium magnesiate K2MgR4(PMDETA)2. Having optimised these systems, substrate scope was examined to probe the range and robustness of 18-crown-6/K2MgR4(PMDETA)2 as a catalyst. A wide series of alkynols, including terminal and internal alkynes which contain a variety of potentially reactive functional groups, were cyclised. In comparison to previously reported monometallic systems, bimetallic 18-crown-6/K2MgR4(PMDETA)2 displays enhanced reactivity towards internal alkynol-cyclisation. Kinetic studies revealed an inhibition effect of substrate on the catalysts via adduct formation and requiring dissociation prior to the rate limiting cyclisation step.