Research Seminar: Exploring and Exploiting New Reactivity of Alkyl-Tricarbastannatranes in Lewis Acid and Transition Metal CatalysisExport this event to calendar

Wednesday, January 18, 2017 — 11:00 AM EST

Presented by: ​Eric FillionDepartment of Chemistry, University of Waterloo, Waterloo, Ontario, Canada

My research group has recently characterized the structure and determined the Lewis acidity of tricarbastannatranes [N(CH2CH2CH2)3Sn]+(X)- (X = BF4, SbF6, B[(3,5-(CF3)2(C6H3)]4). The tin complexes were prepared by the reaction of N(CH2CH2CH2)3SnCl with AgBF4, AgSbF6, and AgB[(3,5-(CF3)2(C6H3)]4, respectively (Figure 1). In parallel, the reactivity of hypervalent alkyl-tricarbastannatranes with B(C6F5)3 was investigated; the axial alkyl ligand is transferred from the tin center to the boron center, with the exception of isopropyl, for which hydride transfer was observed. Furthermore, it has been demonstrated that [N(CH2CH2CH2)3Sn]+[MeB(C6F5)3]- promotes the conjugate addition of alkyl-tricarbastannatranes (alkyl and hydride) to electron-deficient alkenes such as benzylidene Meldrum’s acids; detailed mechanistic studies will be presented.[1,2,3] In addition, it has been shown that pentacoordinated alkyl-tricarbastannatranes efficiently transmetalate with cationic Pd(II) centers,[4] and cationic Rh(I) catalysts (Figure 1).

Figure. 1 Alkyl-tricarbastannatranes Reactivity

Figure. 1 Alkyl-tricarbastannatranes Reactivity

References:

[1] A. Kavoosi; E. Fillion Angew. Chem. Int. Ed., 2015, 54, 5488-5492.

[2] E. Fillion, A. Kavoosi, K. Nguyen, C. Ieritano Chem. Commun. 2016, 52, 12813-12816.

[3] P. Simidzija, M. J. Lecours, R. A. Marta, V. Steinmetz, T. B. McMahon, E. Fillion, W. S. Hopkins Inorg. Chem. 2016, 55, 9579-9585.

[4] E. Fillion; N. J. Taylor J. Am. Chem. Soc., 2003, 125, 12700-12701.

Location 
School of Pharmacy
PHR 1008
10A Victoria Street South

Kitchener, ON N2G 1C5
Canada

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