A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones by the intermolecular coupling reactions of N-acyliminium ions with unactivated olefins
نویسندگان
چکیده
A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones has been achieved by the coupling reactions of N-acyliminium ions produced from 3-hydroxyisoindol-1-ones or 5-hydroxy-1-pyrrol-2-ones with unactivated olefins in the presence of BF(3)·OEt(2) at room temperature. For most of the olefins, the reactions afforded the C(sp3)-C(sp2) cross-coupling products, but for the α-methylstyrene and 1-hexene, the C(sp3)-C(sp3) cross-coupling products were obtained.
منابع مشابه
Synthesis of 9Z-9-substituted retinoic acids by palladium catalyzed coupling reaction of a vinyl triflate with alkenyl stannanes.
Palladium catalyzed cross coupling reactions of a vinyl triflate intermediate and various alkenyl stannanes afforded trisubstituted Z-olefins stereoselectively in high yields. These olefins were then converted to the corresponding 9Z-retinoic acids via Horner-Emmons reaction and subsequent basic hydrolysis in excellent yields.
متن کاملElectrocatalytic intermolecular olefin cross-coupling by anodically induced formal [2+2] cycloaddition between enol ethers and alkenes.
Electrochemical reactions have proven to be valuable means for reversing the polarity of alkenes and triggering radical anionor radical cation-based cyclizing reactions. Anodic olefin coupling initiated by oxidation of electronrich olefins can provide powerful tools for achieving intramolecular cyclization reactions and building new ring systems. In this case, several combinations of olefins ca...
متن کاملNickel-Catalyzed Coupling Reactions of Alkenes.
Several reactions of simple, unactivated alkenes with electrophiles under nickel(0) catalysis are discussed. The coupling of olefins with aldehydes and silyl triflates provides allylic or homoallylic alcohol derivatives, depending on the supporting ligands and, to a lesser extent, the substrates employed. Reaction of alkenes with isocyanates yields N-alkyl acrylamides. In these methods, alkenes...
متن کاملCobalt-catalyzed directed C–H alkenylation of pivalophenone N–H imine with alkenyl phosphates
A cobalt–N-heterocyclic carbene (NHC) catalyst efficiently promotes an ortho C–H alkenylation reaction of pivalophenone N–H imine with an alkenyl phosphate. The reaction tolerates various substituted pivalophenone N–H imines as well as cyclic and acyclic alkenyl phosphates. Introduction Transition-metal-catalyzed, directing group-assisted arene C–H activation reactions have been extensively stu...
متن کاملInsertion of alkynes into Pt-X bonds of square planar [PtX2(N^N)] (X = Cl, Br, I) complexes.
The reactivity with acetylene of [PtX2(Me2phen)] (X = Cl, Br, I) complexes has been investigated. Whereas the chlorido species [PtCl2(Me2phen)] exhibits negligible reactivity at short reaction times, the bromido and iodido species [PtBr2(Me2phen)] and [PtI2(Me2phen)] lead initially to formation of Pt(II) five-coordinate complexes, [PtX2(η(2)-CH≡CH)(Me2phen)], that evolve to four-coordinate alke...
متن کامل