Hydrogermylation initiated by trialkylborohydrides: a living anionic mechanism

Chem Commun (Camb). 2022 Dec 15;58(100):13979-13982. doi: 10.1039/d2cc05567h.

Abstract

Sodium trialkylborohydrides were found to be initiators of selective hydrogermylation of aromatic alkenes. Addition of phenylgermane and diphenylgermane in the presence of 10 mol% of NaHB(sec-Bu)3 proceeded in a highly selective manner to give - in contrast to the analogous hydrosilylation process - β-germylated products. The nature of this process was explained with the aid of DFT calculations and it was proposed that the mechanism proceeds via a trisubstituted germanide anion whose attack on the terminal vinyl carbon is the source of selectivity.

MeSH terms

  • Alkenes*
  • Anions
  • Density Functional Theory

Substances

  • Alkenes
  • Anions