Selective hydroboration of alkenes and alkynes in the presence of aldehydes and ketones

George Kabalka, Su Yu, Nan Sheng Li

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

The reactions of terminal alkenes in the presence of ketones or aldehydes with a variety of borane reagents have been investigated. It was found that the selective hydroboration of a terminal alkene in the presence of a ketone or an aldehyde is most efficient when dicyclohexylborane is used as the hydroborating agent. The hydroboration of olefinic ketones and olefinic aldehydes with dicyclohexylborane generates the corresponding hydroxyaldehydes and hydroxyketones in good yields after oxidation with sodium perborate. The hydroboration of alkynyl ketones and alkynyl aldehydes with dicyclohexylborane yields the corresponding olefinic carbonyl compounds after protonation, or dicarbonyl compounds after oxidation.

Original languageEnglish (US)
Pages (from-to)800-805
Number of pages6
JournalCanadian Journal of Chemistry
Volume76
Issue number6
DOIs
StatePublished - Jan 1 1998

Fingerprint

Alkynes
Alkenes
Ketones
Aldehydes
Olefins
sodium perborate
Boranes
Carbonyl compounds
Oxidation
Protonation
Sodium

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

Cite this

Selective hydroboration of alkenes and alkynes in the presence of aldehydes and ketones. / Kabalka, George; Yu, Su; Li, Nan Sheng.

In: Canadian Journal of Chemistry, Vol. 76, No. 6, 01.01.1998, p. 800-805.

Research output: Contribution to journalArticle

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