Organosodium compounds for catalytic cross-coupling

Sobi Asako, Hirotaka Nakajima, Kazuhiko Takai

Research output: Contribution to journalArticlepeer-review

37 Citations (Scopus)


Sodium is the most abundant alkali metal in the Earth’s crust and the ocean. However, organosodium compounds have long been considered inferior to organolithium compounds, which have instead dominated synthetic organic chemistry during the last century. Despite being largely neglected because of their reactive nature, it is worth re-exploring organosodium chemistry, in light of the growing demand for sustainable syntheses without recourse to less abundant elements such as lithium. Herein, we demonstrate that, contrary to common belief, organosodium compounds can be easily prepared from aryl chlorides or (hetero)arenes and easy-to-handle sodium dispersion and, after being transmetallated to the corresponding zinc and boron compounds, they readily participate in the Negishi and Suzuki–Miyaura cross-coupling reactions, fundamental carbon–carbon bond-forming reactions in organic synthesis. Direct coupling reactions with organosodium species were also possible.

Original languageEnglish
Pages (from-to)297-303
Number of pages7
JournalNature Catalysis
Issue number4
Publication statusPublished - Apr 1 2019

ASJC Scopus subject areas

  • Catalysis
  • Bioengineering
  • Biochemistry
  • Process Chemistry and Technology


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