Easy access to nucleophilic boron through diborane to magnesium boryl metathesis

Anne Frédérique Pécharman, Annie L. Colebatch, Michael S. Hill, Claire L. McMullin, Mary F. Mahon, Catherine Weetman

Research output: Contribution to journalArticlepeer-review

78 Citations (SciVal)


Organoboranes are some of the most synthetically valuable and widely used intermediates in organic and pharmaceutical chemistry. Their synthesis, however, is limited by the behaviour of common boron starting materials as archetypal Lewis acids such that common routes to organoboranes rely on the reactivity of boron as an electrophile. While the realization of convenient sources of nucleophilic boryl anions would open up a wealth of opportunity for the development of new routes to organoboranes, the synthesis of current candidates is generally limited by a need for highly reducing reaction conditions. Here, we report a simple synthesis of a magnesium boryl through the heterolytic activation of the B-B bond of bis(pinacolato)diboron, which is achieved by treatment of an easily generated magnesium diboranate complex with 4-dimethylaminopyridine. The magnesium boryl is shown to act as an unambiguous nucleophile through its reactions with iodomethane, benzophenone and N,N′-di-isopropyl carbodiimide and by density functional theory.

Original languageEnglish
Article number15022
Pages (from-to)1-7
Number of pages7
JournalNature Communications
Early online date7 Apr 2017
Publication statusPublished - 7 Apr 2017

ASJC Scopus subject areas

  • General Chemistry
  • General Biochemistry,Genetics and Molecular Biology
  • General Physics and Astronomy


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