Electrophilic C−H Zincation and Alumination

C−H metalation is the most efficient method to prepare organo–metallic complexes that are ubiquitous nucleophiles. Virtually all transition metal-free C–H metalation routes to form Al/Zn organometallics require stoichiometric, strong Brønsted bases. Herein, we present our studies developing a catalytic in amine/ammonium salt (R3N/[(R3N)H]+) C–H metalation process to form aryl-zinc and aryl-aluminium complexes.

This includes C-H metalation using M-H complexes and transfer metalation using M-Me complexes. Key to the success of this approach is coupling an endergonic electrophilic C-H metalation step with a sufficiently exergonic protonlysis step. This talk will also present: (i) our mechanistic studies into the details of this process which indicated ligand non-innocence can be key, and (ii) the combination of this C-H metalation with subsequent in-situ transformations to realise Al/Zn catalysed C-H bond functionalisations. Finally, we will present our serendipitous discovery of an unusual sp3 C-H alumination.

Host: Angelo Frei, angelo.frei@york.ac.uk.  

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