Despite significant synthetic potential, transition metal catalysis of cationic molecules is underdeveloped. We are developing general and efficient transition metal-catalyzed transformations of cationic intermediates and substrates to solve long-standing challenges in organic synthesis. In one area, we have developed an enantioselective, copper-catalyzed alkynylation of cyclic oxocarbenium ion intermediates to enable efficient preparation of substituted oxygen heterocycles from readily available, racemic cyclic acetals. We have also developed a nickel-catalyzed cross coupling of benzylic ammonium salts with aryl boronic acids. This method enables efficient access to diarylmethylene products in high yields with wide functional group tolerance under extremely mild conditions. Further, it converts chiral benzylic amine derivatives to highly enantioenriched diarylethanes via a stereospecific coupling.

Transition metal catalysis of cationic intermediates and substrates

245th National Meeting (2013)

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