Theoretical investigation into the palladium-catalyzed silaboration of pyridines

Alireza Ariafard; Elham S. Tabatabaie; Ali T. Monfared; Shirin H.A. Assar; Christopher J.T. Hyland; Brian F. Yates

doi:10.1021/om2008106

Theoretical investigation into the palladium-catalyzed silaboration of pyridines

Alireza Ariafard^*, Elham S. Tabatabaie, Ali T. Monfared, Shirin H.A. Assar, Christopher J.T. Hyland, Brian F. Yates

^*Corresponding author for this work

Research School of Chemistry

Research output: Contribution to journal › Article › peer-review

17 Citations (SciVal)

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.

Original language	English
Pages (from-to)	1680-1687
Number of pages	8
Journal	Organometallics
Volume	31
Issue number	5
DOIs	https://doi.org/10.1021/om2008106
Publication status	Published - 12 Mar 2012

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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.",

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AU - Ariafard, Alireza

AU - Tabatabaie, Elham S.

AU - Monfared, Ali T.

AU - Assar, Shirin H.A.

AU - Hyland, Christopher J.T.

AU - Yates, Brian F.

PY - 2012/3/12

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AB - 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.

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Theoretical investigation into the palladium-catalyzed silaboration of pyridines

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