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Cobalt-Catalyzed Green Cross-Dehydrogenative C(sp2)-H/P-H Coupling Reactions

  • Mikhail Khrizanforov
  • Sofia Strekalova
  • Vera Khrizanforova
  • Alexey Dobrynin
  • Kirill Kholin
  • Tatyana Gryaznova
  • Valeriya Grinenko
  • Aidar Gubaidullin
  • M. K. Kadirov
  • Yulia Budnikova
Original Paper

Abstract

Joined electrolysis of arenes (benzene or coumarin derivatives) and diethyl-H-phosphonate (EtO)2P(O)H in the presence of [CoCl2(bpy)] catalyst (5%) in an ethanol-aqueous solution in reductive conditions allows obtaining the desired products in a single step by aromatic C–H bonds phosphonation with yields up to 70%. The only by-product is hydrogen; the reaction proceeds at room temperature and does not require specially added reducing agents and oxidants or other initiators. Radical mechanism has been confirmed for the catalytic reaction proceeding via bicobalt phosphonates with Co–P bond, the structure of which also has been identified.

Keywords

Green chemistry Cobalt catalyst C–P bond formation Electrosynthesis 

Notes

Acknowledgements

This work was supported by the Russian Science Foundation No. 14-23-00016.

Compliance with Ethical Standards

Conflict of interest

There are no conflicts to declare.

Supplementary material

11244_2018_1014_MOESM1_ESM.doc (3.6 mb)
Supplementary material 1 (DOC 3639 KB)
11244_2018_1014_MOESM2_ESM.cif (1.1 mb)
Supplementary material 2 (CIF 1173 KB)
11244_2018_1014_MOESM3_ESM.pdf (177 kb)
Supplementary material 3 (PDF 176 KB)

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Authors and Affiliations

  1. 1.A. E. Arbuzov Institute of Organic and Physical ChemistryKazan Scientific Center of Russian Academy of SciencesKazanRussian Federation

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