Development of base-metal-catalyzed reactions applicable for new design of organic semiconductor materials

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In previous study I learned in the presence of FeCl2 and PPh3 as catalyst, magnesium/LiCl as a reductant and 1,2-dichloropropane as a mild oxidant, reaction occurred via an organometallic intermediate whereas the stained 1,4-dihydropentalene framework was formed. Then I extended the synthesis for more conjugated dithiophenes using iron-catalyzed tandem tetra-annulation strategy with much higher level of HOMO energy. Besides, well-developed iron-catalyzed annulative carbomagnesiation method was found to be highly applicable for synthesizing derivatized 1H-indenes, dihydro-s-indacenes, and carbon-bridged oligo p-phenylenevinylene congeners with spiro centers, which suggests us prospective work to construct an extended 1,4-dihydropentalene framework with multi-spiro-centers.