Journal article

Reductive Activation and Hydrofunctionalization of Olefins by Multiphoton Tandem Photoredox Catalysis

Milena L Czyz, Mitchell S Taylor, Tyra H Horngren, Anastasios Polyzos

ACS Catalysis | AMER CHEMICAL SOC | Published : 2021

Abstract

The conversion of olefin feedstocks to architecturally complex alkanes represents an important strategy in the expedient generation of valuable molecules for the chemical and life sciences. Synthetic approaches are reliant on the electrophilic activation of unactivated olefins, necessitating functionalization with nucleophiles. However, the reductive functionalization of unactivated and less activated olefins with electrophiles remains an ongoing challenge in synthetic chemistry. Here, we report the nucleophilic activation of inert styrenes through a photoinduced direct single electron reduction to the corresponding nucleophilic radical anion. Central to this approach is the multiphoton tand..

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Grants

Awarded by ARC


Funding Acknowledgements

M.L.C. acknowledges the ARC Industrial Transformation Training Centre Post-Doctoral Fellowship; T.H.H. acknowledges the University of Melbourne, Melbourne Research Scholarship (MRS); A.P. acknowledges the University of Melbourne and CSIRO for the joint Establishment Grant and the ARC (IC1701000020). The authors acknowledge Prof. Trevor Smith and Dr Siobhan Bradley for their generous assistance with the transient absorption spectroscopy studies and Amanda Lee Bunyamin for assistance with the synthesis of olefin substrates.