Mechanism and Applications of the Photoredox Catalytic Coupling of Benzyl Bromides |
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| Authors: | Gyurim Park Seung Yeon Yi Jaehun Jung Dr Eun Jin Cho Dr Youngmin You |
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| Institution: | 1. Department of Food Science and Engineering, Ewha Womans University, Seoul, Republic of Korea;2. Department of Chemistry and Nano Science, Ewha Womans University, Seoul, Republic of Korea;3. Department of Applied Chemistry, Hanyang University, Ansan, Republic of Korea;4. Department of Chemistry, Chung-Ang University, Seoul, Republic of Korea;5. Division of Chemical Engineering and Materials Science, Ewha Womans University, Seoul, Republic of Korea |
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| 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 IrIII complex 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. |
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| Keywords: | bibenzyl Hantzsch ester organic chemistry photochemistry radical coupling |
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