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Science China Chemistry

, Volume 62, Issue 11, pp 1519–1524 | Cite as

Visible-light-mediated external-reductant-free reductive cross coupling of benzylammonium salts with (hetero)aryl nitriles

  • Meng Miao
  • Li-Li Liao
  • Guang-Mei Cao
  • Wen-Jun ZhouEmail author
  • Da-Gang YuEmail author
Articles

Abstract

Herein we report a novel visible-light-mediated external reductant-free reductive cross coupling for the construction of C sp2–C sp3 bonds. A variety of benzylammonium salts underwent selective coupling with (hetero)aryl nitriles to deliver important diarylmethanes under mild reaction conditions. Importantly, photocatalysts can be omitted for many cases, which might involve the electron donor acceptor (EDA) complex. Mechanistic studies indicated benzylic radicals might be involved as the key intermediates. Moreover, the in situ generated NMe3 via cleavage of C–N bond in ammonium salts acts as the electron donor, thus avoiding the use of external-reductant.

Keywords

reductive cross coupling visible light external-reductant-free 

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Notes

Acknowledgements

This work was supported by the National Natural Science Foundation of China (21772129, 21801176), the The National Basic Research Program of China from the Minstry of Science and Technology of China (2015CB856600), Sichuan Science and Technology Program (2019YJ0379), Neijiang Normal University (KF10076) and the Fundamental Research Funds for the Central Universities (YJ201516).

Conflict of interest The authors declare that they have no conflict of interest.

Supplementary material

11426_2019_9597_MOESM1_ESM.pdf (3.6 mb)
Visible-light-mediated external-reductant-free reductive cross coupling of benzylammonium salts with (hetero)aryl nitriles

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Copyright information

© Science China Press and Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of ChemistrySichuan UniversityChengduChina
  2. 2.College of Chemistry and Chemical EngineeringNeijiang Normal UniversityNeijiangChina

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