Synfacts 2009(2): 0136-0136  
DOI: 10.1055/s-0028-1087572
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Intramolecular Heck Route to 5-, 6-, and 7-Membered O-Containing Heterocycles

Contributor(s): Victor Snieckus, Josefine Karlsson
S. Samanta, H. Mohapatra, R. Jana*, J. K. Ray*
Indian Institute of Technology, Kharagpur, India
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22. Januar 2009 (online)


Reported is a method to synthesize 2-arylsubstituted tetrahydropyran, tetrahydrofuran and oxepine derivatives via a Pd-catalyzed intra­molecular Heck reaction. The construction of the precursors is achieved from aromatic aldehydes using established indium or Grignard condensation followed by O-allylation. The reported reactions are suitable for substrates with both electron-donating and -withdrawing substituents, except for nitro groups. The scope of the reaction was insufficiently investigated in terms of the different vinylbromides used.