Coupling reactions are a mainstay of organic synthesis, both in research and industrial chemistry.  The current best and most-used coupling reactions, like Suzuki couplings, are limited by their use of strongly basic conditions, which cannot tolerate base-sensitive functional groups.  In these reactions, bases are added to the reaction to activate the boronic acid or ester.  Recently, we reported the expedient synthesis of ammonium organotetrafluorosilicate salts.  These compounds have not been explored as coupling partners until recently and show significant potential.  Initial results show that organotetrafluorosilicates will couple with aryldiazonium salts in the presence of a palladium catalyst, producing easily removable byproducts.  The activated silicon does not require a base additive in order to couple effectively.  This implies that this coupling could work under mildly acidic conditions, however, additional work will need to be undertaken to determine how functional group tolerant this reaction is.  Optimization and substrate scope of this new transformation will be discussed.

Additive-free coupling of ammonium organotetrafluorosilicate salts and aryldiazonium salts

ACS Spring 2022

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