Functionalized tricyclic indene derivatives were synthesized using the iron-mediated cyclocarbonylation of 1,6-diynes.  A series of diynes were formed from the terminal alkynes phenyl acetylene, trimethylsilyl acetylene, and 4-pentyn-1-ol.  Starting from 2-bromobenzaldehyde, the terminal alkynes were added sequentially using both a Sonogashira cross coupling reaction and the nucleophilic addition of the acetylide ion to the aldehyde.  The resulting hydroxy-diynes undergo cyclocarbonylation with iron pentacarbonyl at 125 �C under 50 psi of carbon monoxide to give the (cyclopenta[a]inden-2(8H)-one)tricarbonyliron(0) complexes.  Efforts to demetallate cyclopentadienone complexes using Me3NO are currently in progress.  All synthetic intermediates were all characterized using 1H and 13C NMR, IR, and GC-MS.

Synthesis of functionalized indene-cyclopentadienone iron tricarbonyl complexes

247th National Meeting (2014)

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