One of the most challenging aspects of Suzuki-Miyaura reactions is the stereospecific cross-coupling of sp3 substituted boronic esters with aryl halides. Recently, the host group developed a metal-free, stereospecific cross-coupling reaction of chiral alkyl boronates with electron-rich aromatics, promoted by the use of electrophilic oxidants. This proposal seeks to substantially extend this cross-coupling chemistry through the application of a range of different electrophiles that will not only mediate the cross-coupling process, but also remain in the final product, creating multiple carbon–carbon bonds stereospecifically. In particular, the application of electrophilic organometallic species will be investigated so as to take advantage of the power of metal catalysts in the formation of carbon–carbon bonds. Through the use of this strategy, doubly functionalised enantiopure aromatic compounds may be formed in a very efficient three-component coupling process that utilises readily accessible enantiopure alkyl boronic esters, electron-rich aromatics and catalytically generated organometallic electrophiles.
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