The bromination of vinylboronic acids on alumina

Deborah A. Willis, Michael B. McGinnis, George Kabalka, Richard M. Pagni

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

The reaction of a series of vinylboronic acids with Br2 on alumina has been examined. A mixture of (E)- and (Z)-vinyl bromides was formed in every case by competing mechanisms: (1) SE2 reaction of the surface-complexed vinylboronic acid with Br2 to form the E isomer and (2) anti-elimination of B(OH)3 and Br from the surface-complexed adduct arising by the reaction of vinylboronic acid and Br2 in solution, which affords the Z isomer. As was the case with the comparable iodination reactions, the bromination of the vinylboronic acids synthesized from phenylacetylene and 3,3-dimethyl-1-butyne gave inordinately large amounts of (E)-vinyl halides. Because of steric factors in these examples the anti elimination described above is retarded and a syn elimination occurs preferentially. Experiments were performed to test the mechanisms.

Original languageEnglish (US)
Pages (from-to)35-39
Number of pages5
JournalJournal of Organometallic Chemistry
Volume487
Issue number1-2
DOIs
StatePublished - Feb 8 1995

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bromination
Aluminum Oxide
Halogenation
Alumina
aluminum oxides
elimination
acids
Acids
Isomers
isomers
adducts
halides
bromides
Experiments

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

The bromination of vinylboronic acids on alumina. / Willis, Deborah A.; McGinnis, Michael B.; Kabalka, George; Pagni, Richard M.

In: Journal of Organometallic Chemistry, Vol. 487, No. 1-2, 08.02.1995, p. 35-39.

Research output: Contribution to journalArticle

Willis, Deborah A. ; McGinnis, Michael B. ; Kabalka, George ; Pagni, Richard M. / The bromination of vinylboronic acids on alumina. In: Journal of Organometallic Chemistry. 1995 ; Vol. 487, No. 1-2. pp. 35-39.
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