Recently, an efficient synthetic method towards multisubstituted furans and pyrroles bearing hetero-substituents was reported through metal-catalyzed 1,2-shifts of diverse migrating groups in allenyl systems. However, the introduction of a wide variety of substituents at the 4-position of furans and pyrroles is impossible due to requirement of [1,3]-H shift in these methods. Therefore, the development of an efficient synthetic method for multisubstituted furans and pyrroles bearing 3-heteroatom substituents as well as substituents at the 4-position has been a continuing challenge.
Herein, we report Pd-catalyzed propargyl substitution reactions of propargyl acetates with indium organothiolates for the synthesis of multisubstituted allenyl sulfides. This procedure employed tandem Pd-catalyzed propargyl substitution and cycloisomerization reactions from indium organothiolates and propargyl acetates bearing acyl and imidoyl groups for the synthesis of multisubstituted furans and pyrroles in one-pot.This work was supported by the Human Resource Training Program for Regional Innovation and Creativity through the Ministry of Education and National Research Foundation of Korea (NRF-2015H1C1A1035955)