Alkylation of Aldehyde (Arenesulfonyl)hydrazones with Trialkylboranes

George Kabalka, John T. Maddox, Ekaterini Bogas, Shane W. Kelley

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

(Arenesulfonyl)hydrazone derivatives of aryl aldehydes are readily alkylated by trialkylboranes in the presence of base to generate new organoboranes that may be converted to the corresponding substituted alkanes or alcohols depending upon the reaction conditions chosen. Both tosyl- and trisylhydrazone derivatives can be utilized in the reaction, which tolerates a variety of functional groups, making it a versatile alternative to both the Grignard and Suzuki-coupling reactions.

Original languageEnglish (US)
Pages (from-to)3688-3695
Number of pages8
JournalJournal of Organic Chemistry
Volume62
Issue number11
DOIs
StatePublished - Jan 1 1997
Externally publishedYes

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Hydrazones
Alkylation
Aldehydes
Derivatives
Alkanes
Functional groups
Alcohols

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Alkylation of Aldehyde (Arenesulfonyl)hydrazones with Trialkylboranes. / Kabalka, George; Maddox, John T.; Bogas, Ekaterini; Kelley, Shane W.

In: Journal of Organic Chemistry, Vol. 62, No. 11, 01.01.1997, p. 3688-3695.

Research output: Contribution to journalArticle

Kabalka, George ; Maddox, John T. ; Bogas, Ekaterini ; Kelley, Shane W. / Alkylation of Aldehyde (Arenesulfonyl)hydrazones with Trialkylboranes. In: Journal of Organic Chemistry. 1997 ; Vol. 62, No. 11. pp. 3688-3695.
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