72310-67-9Relevant articles and documents
Dual Oxidation State Tandem Catalysis in the Palladium-Catalyzed Isomerization of Alkynyl Epoxides to Furans
Arroniz, Carlos,Chaubet, Guilhem,Anderson, Edward A.
, p. 8290 - 8295 (2018/09/06)
A two-catalyst system consisting of different oxidation states of palladium is described, which mediates the isomerization of alkynyl epoxides to furans. In a process termed dual oxidation state tandem catalysis , a multistep isomerization pathway is delineated in which the different metal oxidation states and ligands play independent mechanistic roles, but which, in combination, enable the use of milder reaction conditions and lower catalyst loadings than a single catalyst in isolation. In the present context, this rare example of a homobimetallic catalytic transformation provides a mild, scalable, and atom-efficient route for furan synthesis.
On the curious oxidations of 2-furylethanols
Hayes, Simon J.,Knight, David W.,Smith, Andrew W.T.,O'Halloran, Mark J.
scheme or table, p. 720 - 723 (2010/04/05)
Rather than giving the corresponding aldehyde or carboxylic acid, Jones oxidation of 5-substituted-2-furylethanols gives rise to high yields of the corresponding dihydro-2-(2-oxoethyl)furan-3(2H)-ones, following Achmatowicz-type oxidative ring opening and subsequent reclosure by a 5-exo Michael addition of the pendant hydroxy group to the enedione function. Other oxidation methods such as a Swern reaction give lower yields of the same products while magnesium perphthalate tends to yield the intermediate enediones, and IBX tends to yield the furyl aldehydes.
Furan-terminated N-acyliminium ion initiated cyclizations in alkaloid synthesis
Tanis, Steven P.,Deaton, Melissa V.,Dixon, Lisa A.,McMills, Mark C.,Raggon, Jeffrey W.,Collins, Mark A.
, p. 6914 - 6928 (2007/10/03)
A study of the utility of furan-terminated W-acyliminium ion initiated cyclizations for the synthesis of linearly fused alkaloid precursors (Figure 2) is presented. The outcome of the cyclization event depends on the position of furan tether attachment (2 vs 3), tether length, and furan 5-substituent (R = H, CH3, Ar). 3-Substituted furans cyclized to form 6- and 7-membered ring containing furans 35-38,50, and 51 in good to excellent yields. 2-Substituted furans closed to form only 6-membered rings; however, the products obtained were a function of the furan 5-substituent. The 5-H furans 17 and 18 led exclusively to the corresponding furans 21 and 22, while the 5-CH3-furans 42 and 43 gave only diketone containing compounds 44 and 45. 5-Arylfurans 66-71 provided mixtures of furan- and diketone-containing products 72-83, with the ratio related to the substitution on the phenyl moiety. A preparation of epilupinine 10 is also discussed.
