Many recent studies have established that mixed-metal formulations which combine zinc with an alkali-metal are versatile organometallic reagents in synthesis, offering better chemo- and regio-selectivities than conventional monometallic reagents. Despite a large number of synthetic organic studies having utilising these reagents, the key factors governing their reactions still remain to be elucidated and fully understood. We have approached this intriguing area from more of an inorganic/structural/metal perspective. This talk will present results from our work that provide new insights into the true identities of the organometallic intermediates involved in these reactions prior to any electrophilic interception step focussing on deprotonation and metal-halogen exchange processes. By using a combination of X-ray crystallography, NMR spectroscopy and DFT calculations, we will discuss how the structures of, and the bonding within these isolated metallo intermediates, can help to rationalise the unique regioselectivities observed in these fundamental organic transformations.

Organozinc reagents: Structural tailoring for mixed-metal applications

241st National Meeting (2011)

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