Collect. Czech. Chem. Commun. 2010, 75, 313-332
Published online 2010-03-15 09:25:45

Synthesis of (E)-6-alkenylpurines via Pd-catalyzed stannation/protodestannation tandem process of alkynylpurines

Martin Klečka, Martin Křováček, Tomáš Tobrman* and Dalimil Dvořák

Department of Organic Chemistry, Institute of Chemical Technology, Prague, Technická 5, 166 28 Prague 6, Czech Republic


A methodology for the synthesis of (E)-6-alkenylpurines, starting from 6-iodopurines, based on a Pd-catalyzed stannation/protodestannation protocol, is described. The alkynylation reactions were catalyzed by Pd(OAc)2/PPh3 in acetonitrile. The Pd-catalyzed stannation itself provided a mixture of Z regioisomers but following protodestannation using TFA induces Z to E isomerization giving (E)-6-alkenylpurines. The reactivity of other 2- and 8-alkynyl purines has also been studied.

Keywords: Alkynes; Hydrostannation; Isomerization; Purine; Protodestannation.

References: 56 live references.