2011
DOI: 10.1002/hc.20709
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Reaction ofo‐(HSiR2)(BMes2)C6H4with a fluoride ion: Fluoride attack at silicon and hydride transfer from silicon to boron to form FSi⋅⋅⋅HB interaction

Abstract: Reactions of o‐(HSiR2)(BMes2)C6H4 (R = Me (3a), Ph (3b)) with a fluoride ion afford [o‐(FSiR2)(HBMes2)C6H4]− (R = Me (5a), Ph (5b)), which involve the FSi⋅⋅⋅HB interaction to render the silicon atom pentacoordinate. The FSi⋅⋅⋅HB interaction in 5a was confirmed by X‐ray crystallographic analysis and “atoms‐in‐molecules” (AIM) analysis. © 2011 Wiley Periodicals, Inc. Heteroatom Chem 22:471–475, 2011; View this article online at http://wileyonlinelibrary.com. DOI 10.1002/hc.20709

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Cited by 8 publications
(4 citation statements)
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“…The resulting barrier is 22.1 kcal/mol, significantly lower than that of Ia. This mechanism agrees with the push–pull mechanism suggested by Kawachi. , …”
Section: Resultssupporting
confidence: 68%
See 1 more Smart Citation
“…The resulting barrier is 22.1 kcal/mol, significantly lower than that of Ia. This mechanism agrees with the push–pull mechanism suggested by Kawachi. , …”
Section: Resultssupporting
confidence: 68%
“…This mechanism agrees with the push−pull mechanism suggested by Kawachi. 7,20 In the reaction pathway Ic, the alcohol approaches from a different angle. The proton from the hydroxyl group comes near to one of the phenyl rings of a mesityl group connected to the boron center.…”
Section: ■ Results and Discussionmentioning
confidence: 91%
“…The reaction of o-(silyl)(dimesitylboryl)benzene with KF produced a borohydride species through the nucleophilic attack of fluoride at the silicon and the hydride transfer from silicon to boron. 40,41 Scheme 8 Alkaline earth metal catalysed dehydrocoupling of amines with silane.…”
Section: Boron and Aluminummentioning
confidence: 99%
“…ortho ‐(Hydrosilyl)(boryl)benzenes 1 a and 1 b also reacted with KF in the presence of a cryptand to form hydridoborates 3 , which involved the unprecedented intramolecular FSi⋅⋅⋅HB interaction (Scheme ) 6d. The nucleophilic attack of a fluoride ion on the silicon atom triggers the hydride transfer from the silicon center onto the boron atom.…”
Section: Introductionmentioning
confidence: 99%