Rhodium-catalyzed dehydrogenative borylation of aliphatic terminal alkenes with pinacolborane

Masao Morimoto, Tomoya Miura, Masahiro Murakami

Research output: Contribution to journalArticlepeer-review

39 Citations (Scopus)

Abstract

Aliphatic terminal alkenes react with pinacolborane at ambient temperature to afford dehydrogenative borylation compounds as the major product when iPr-Foxap is used as the ligand with cationic rhodium(I) in the presence of norbornene, which acts as the sacrificial hydrogen acceptor. The reaction is applied to the one-pot syntheses of aldehydes and homoallylic alcohols from aliphatic terminal alkenes. Crazy like a fox: Aliphatic terminal alkenes react with pinacolborane at ambient temperature in the presence of [Rh(cod)2]BF4/iPr-Foxap and norbornene to produce dehydrogenative borylation compounds as the major product. The reaction is applied to the one-pot syntheses of aldehydes and homoallylic alcohols from aliphatic terminal alkenes. cod=1,5-cyclooctadiene.

Original languageEnglish
Pages (from-to)12659-12663
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number43
DOIs
Publication statusPublished - Oct 1 2015
Externally publishedYes

Keywords

  • alkenes
  • boron
  • reaction mechanisms
  • rhodium
  • synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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