An enantioselective variant of an efficient and general iron-catalyzed Suzuki-Miyaura protocol for cross coupling alkyl halides and unactivated aryl-boronic esters is reported. Using chiral, C<sub>2</sub>-symmetric cyanobisoxazoline ligands, secondary alkyl halides underwent cross coupling with aryl-boronic esters to furnish enantiomerically enriched cross coupled products in good yields. While nickel-catalyzed enantioselective Suzuki-Miyaura cross coupling reactions have been reported, an enantioselective iron-catalyzed variant of the reaction has, until now, remained elusive. Initial mechanistic investigation into the reaction is consistent with a stereoconvergent mechanism involving radical intermediates rather than a kinetic resolution reaction. The effect of altering the chiral cyanobisoxazoline ligand as well as an exploration of the substrate scope will be presented.

Enantioselective Suzuki-Miyaura cross coupling of alkyl halides and unactivated boronic esters

256th National Meeting (2018)

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