Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Alkylation and Allylation of Lithium Arylborates Factors Affecting the Di/Mono Substitution Ratio$^\dag$

  • Published : 1987.10.20
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Abstract

Alkylation and allylation of arylborates give mono(ipso) and/or di(ortho and ipso) substitution products. Those factors which promote polarization or ionization of alkylating agents favor di substitution. The ${\sigma}$-type(ipso) substitution reaction of arylborates involves direct interaction of the carbon-boron bonds rather than predissociation of arylborates into aryllithiums and boranes.

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References

  1. Organic Synthesis via Boranes H. C. Brown
  2. Organometallics in Organic Synthesis v.1 E. Negishi
  3. J. Org. Chem. v.29 R. Damico
  4. Angew. Chem. v.70 G. Wittig
  5. J. Chem. Soc., Chem. Commun. E. Negishi;A. Abramovitch;R. E. Merrill
  6. J. Chem. Soc., Chem. Commun. E. Negishi;R. E. Merrill

Cited by

  1. Electrophilic Aromatic Substitutions of Aryltrifluoroborates with Retention of the BF3– Group: Quantification of the Activating and Directing Effects of the Trifluoroborate vol.135, pp.16, 1987, https://doi.org/10.1021/ja4017655