Face to face activation of a phenylselenium borane with α,β-unsaturated carbonyl substrates: facile synthesis of C-Se bonds

Chem Commun (Camb). 2014 Aug 7;50(61):8420-3. doi: 10.1039/c4cc02098g.

Abstract

Activated olefins directly react with a phenylselenium borane, at room temperature, without any metal or organocatalytic assistance. Up to 10 examples of β-(phenylseleno) substituted ketones and aldehydes have been prepared and theoretical evidence for the mechanism opens up non-existing pathways to create C-heteroatom bonds as a general tool.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Alkenes / chemistry
  • Boranes / chemistry*
  • Carbon / chemistry
  • Ketones / chemistry*
  • Molecular Conformation
  • Selenium / chemistry
  • Temperature
  • Thermodynamics

Substances

  • Aldehydes
  • Alkenes
  • Boranes
  • Ketones
  • Carbon
  • Selenium