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Theoretical investigation into the palladium-catalyzed silaboration of pyridines

Journal Article


Abstract


  • The palladium-catalyzed silaboration of pyridines has been investigated with the use of density functional theory. The results predict a very interesting dearomatization step in the reaction mechanism which is surprisingly facile due to the formation of a very strong covalent bond between nitrogen and boron in the product. Our calculations show that the regioselectivity of the final product is governed by a mixture of electronic and steric effects, and our predicted outcomes are in agreement with the experimental results.

UOW Authors


  •   Ariafard, Alireza (external author)
  •   Tabatabaie, Elham S. (external author)
  •   Monfared, Ali T. (external author)
  •   Assar, Shirin H. A. (external author)
  •   Hyland, Christopher
  •   Yates, Brian F. (external author)

Publication Date


  • 2012

Citation


  • Ariafard, A., Tabatabaie, E. S., Monfared, A. T., Assar, S. H. A., Hyland, C. J. T. & Yates, B. F. (2012). Theoretical investigation into the palladium-catalyzed silaboration of pyridines. Organometallics, 31 (5), 1680-1687.

Scopus Eid


  • 2-s2.0-84858112864

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/2319

Has Global Citation Frequency


Number Of Pages


  • 7

Start Page


  • 1680

End Page


  • 1687

Volume


  • 31

Issue


  • 5

Place Of Publication


  • United States

Abstract


  • The palladium-catalyzed silaboration of pyridines has been investigated with the use of density functional theory. The results predict a very interesting dearomatization step in the reaction mechanism which is surprisingly facile due to the formation of a very strong covalent bond between nitrogen and boron in the product. Our calculations show that the regioselectivity of the final product is governed by a mixture of electronic and steric effects, and our predicted outcomes are in agreement with the experimental results.

UOW Authors


  •   Ariafard, Alireza (external author)
  •   Tabatabaie, Elham S. (external author)
  •   Monfared, Ali T. (external author)
  •   Assar, Shirin H. A. (external author)
  •   Hyland, Christopher
  •   Yates, Brian F. (external author)

Publication Date


  • 2012

Citation


  • Ariafard, A., Tabatabaie, E. S., Monfared, A. T., Assar, S. H. A., Hyland, C. J. T. & Yates, B. F. (2012). Theoretical investigation into the palladium-catalyzed silaboration of pyridines. Organometallics, 31 (5), 1680-1687.

Scopus Eid


  • 2-s2.0-84858112864

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/2319

Has Global Citation Frequency


Number Of Pages


  • 7

Start Page


  • 1680

End Page


  • 1687

Volume


  • 31

Issue


  • 5

Place Of Publication


  • United States