The Suzuki reaction has become a mainstay of the pharmaceutical industry for the formation of planar “2D” biaryl structures. In some cases, chiral alkyl nucleophiles (e.g. 2) can be used to access “3D” benzylic stereocentres (e.g. 3) (Scheme 1A). However, this approach is compromised by slow transmetallation and competing β-hydride elimination, which leads to isomeric side-products.1 An “ideal” (but poorly developed) alternate approach is to form benzylic stereocentres directly via the enantioselective addition of aryl C-H bonds (4) across alkenes (5). This approach has been pursued by the Bower group, who recently reported enantioselective Ir-catalysed hydroarylations of alkenes with acetanilides to provide tertiary benzylic stereocenters.2 The focus of my work has been to broaden the scope of this methodology by designing new chiral catalyst systems (Scheme 1B). I have developed enantioselective protocols that provide tertiary benzylic stereocentres via the hydroarylation of mono-substituted alkenes 7 with a wide range of benzenoid and heterocyclic (6) arenes (Scheme 1C). I have also achieved exciting preliminary results which show that enantioenriched quaternary stereocentres can be accessed by hydroarylation of 1,1-disubstituted alkenes.

Development of an asymmetric alkene hydroheteroarylation methodology

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ACS Fall 2022

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