Uncatalyzed Carboboration of Seven-Membered-Ring trans-Alkenes

Formation of Air-Stable Trialkylboranes

Jillian R. Sanzone, Chunhua T. Hu, Keith Woerpel

Research output: Contribution to journalArticle

Abstract

Seven-membered-ring trans-alkenes undergo rapid, uncatalyzed carboboration reactions to form trialkylboranes as single diastereomers. In contrast with other trialkylboranes, which can ignite in the presence of oxygen, these trialkylboranes are stable in air. Hindered trialkylboranes can undergo reverse hydroboration reactions to form allylic silanes or can be oxidized to afford highly substituted triols. This reaction sequence permits the construction of compounds with up to five consecutive stereocenters. Control experiments and computational studies support a concerted mechanism for the migratory insertion of the alkene into the carbon-boron bond, similar to the mechanism for hydroboration.

Original languageEnglish (US)
Pages (from-to)8404-8407
Number of pages4
JournalJournal of the American Chemical Society
Volume139
Issue number25
DOIs
StatePublished - Jun 28 2017

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Alkenes
Olefins
Air
Silanes
Boron
Carbon
Oxygen
Experiments

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Uncatalyzed Carboboration of Seven-Membered-Ring trans-Alkenes : Formation of Air-Stable Trialkylboranes. / Sanzone, Jillian R.; Hu, Chunhua T.; Woerpel, Keith.

In: Journal of the American Chemical Society, Vol. 139, No. 25, 28.06.2017, p. 8404-8407.

Research output: Contribution to journalArticle

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