Mechanism and Applications of the Photoredox Catalytic Coupling of Benzyl Bromides

Gyurim Park, Seung Yeon Yi, Jaehun Jung, Eun Jin Cho, Youngmin You

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40 Scopus citations

Abstract

The photoredox catalytic coupling of halomethyl arenes to bibenzyl derivatives has been demonstrated. The catalytic protocol employed the Hantzsch ester, potassium phosphate, and a photoactive cyclometalated IrIIIcomplex catalyst. A photochemical quantum yield as high as 20 % was obtained. The catalytic mechanism was investigated in detail by performing photophysical and electrochemical measurements, as well as by quantum chemical calculations. The results suggest that two-electron mediation might be responsible for the improved photon economy. The reaction protocol was compatible with halomethyl arenes that contain a variety of functional groups. Finally, the synthetic utility of our protocol was demonstrated by the preparation of a natural dihydrostilbenoid, brittonin A.

Original languageEnglish
Pages (from-to)17790-17799
Number of pages10
JournalChemistry - A European Journal
Volume22
Issue number49
DOIs
StatePublished - 5 Dec 2016

Keywords

  • bibenzyl
  • Hantzsch ester
  • organic chemistry
  • photochemistry
  • radical coupling

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