Photoredox-Mediated Reaction of gem-Diborylalkenes: Reactivity Toward Diverse 1,1-Bisborylalkanes

Nivesh Kumar, Nadim Eghbarieh, Tamar Stein, Alexander I. Shames, Ahmad Masarwa

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

The use of gem-diborylalkenes as radical-reactive groups is explored for the first time. These reactions provide an efficient and general method for the photochemical conversion of gem-diborylalkenes to rapidly access 1,1-bisborylalkanes. This method exploits a novel photoredox decarboxylative radical addition to gem-diborylalkenes to afford α-gem-diboryl carbon-centered radicals, which benefit from additional stability by virtue of an interaction with the empty p-orbitals on borons. The reaction offers a highly modular and regioselective approach to γ-amino gem-diborylalkanes. Furthermore, EPR spectroscopy and DFT calculations have provided insight into the radical mechanism underlying the photochemistry reaction and the stability of the bis-metalated radicals, respectively.

Original languageEnglish
Pages (from-to)5360-5364
Number of pages5
JournalChemistry - A European Journal
Volume26
Issue number24
DOIs
StatePublished - 24 Apr 2020

Keywords

  • decarboxylation
  • gem-bisboronates
  • organoborones
  • photochemistry
  • radicals

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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