Hydrogenation of Multiple Bonds by Geminal Aminoborane-Based Frustrated Lewis Pairs

Diana Yepes, Pablo Jaque, Israel Fernández

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

The hydrogenation reaction of multiple bonds that is mediated by geminal aminoborane-based frustrated Lewis pairs (FLPs) has been explored by means of density functional theory calculations. It was found that the release of the activated dihydrogen occurred in a concerted, yet highly asynchronous, manner. The physical factors that control the transformation were quantitatively described in detail by using the activation strain model of reactivity in combination with the energy decomposition analysis method. This approach suggested a cooperative double hydrogen-transfer mechanism, which involves the initial migration of the protic (N)H followed by the nucleophilic attack of the (B)H hydride to the carbon atom of the multiple bond. The influence of both the substituents directly attached to the boron atom of the initial FLP and the nature of the multiple bond on the transformation was also investigated.

Original languageEnglish
Pages (from-to)8833-8840
Number of pages8
JournalChemistry - A European Journal
Volume24
Issue number35
DOIs
Publication statusPublished - 21 Jun 2018

Keywords

  • density functional calculations
  • frustrated Lewis pairs
  • hydrogenation
  • multiple bonds
  • reaction mechanisms

ASJC Scopus subject areas

  • Chemistry(all)

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