Abstract
The stereoselective synthesis of (Z)-β-iodovinyl ketones/esters of Morita-Baylis-Hillman (MBH) porphyrin adducts has been achieved with a tandem formation of C - C and C - I bonds in a three-component reaction. The reaction is promoted by MgI 2 as a Lewis acid, as well as an iodine source for a Michael-type addition. The MBH adducts are efficiently oxidized to the corresponding ketones with Dess-Martin periodinane (DMP). These scaffolds are further used in a palladium-catalyzed Sonogashira carbon-carbon coupling reaction to obtain highly extended porphyrin systems.
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