Stereoselective synthesis of: E -3-(arylmethylidene)-5-(alkyl/aryl)-2(3 H)-furanones by sequential hydroacyloxylation-Mizoroki-Heck reactions of iodoalkynes
A modular, stereoselective synthesis of E-3-(arylidene)-5-(alkyl/aryl)-2(3H)-furanones was developed. The methodology features regioselective addition of β-aryl acrylic acids to iodoacetylenes to furnish the Z-acyloxy iodoalkenes. A stereoselective 5-exo-trig Mizoroki-Heck reaction of the acyloxy iodoalkenes generates the target E-2(3H)-furanones. The approach was applied in a formal synthesis of the naturally occurring kinase inhibitor BE-23372M.
Muthusamy, Gopinathan,Pansare, Sunil V.
p. 7971 - 7983
(2018/11/21)
Palladium-catalyzed carbonylative coupling of aryl iodides and benzyl acetylenes to 3-alkylidenefuran-2-ones under mild conditions and its density functional theory modeling
A general and efficient method for the palladium-catalyzed carbonylative coupling of aryl iodides to benzyl acetylenes has been developed. Various furanones have been prepared in excellent yields from their corresponding benzyl acetylenes at room temperat
A general cyclocarbonylation of aryl bromides and triflates with acetylenes: Palladium-catalyzed synthesis of 3-alkylidenefuran-2-ones
Making use of CO: An improved efficient synthesis of 5-aryl-3- alkylidenefuran-2-ones has been developed (see scheme). Starting from readily available (hetero)aryl bromides or aryl triflates and alkynes, furanones were produced in good yields through a do
Wu, Xiao-Feng,Sundararaju, Basker,Anbarasan, Pazhamalai,Neumann, Helfried,Dixneuf, Pierre H.,Beller, Matthias
supporting information; experimental part
p. 8014 - 8017
(2011/09/14)
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