C&CB Department Seminar: Dr. Stephan A. Westcott Department of Chemistry and Biochemistry, Mount Allison University
Oct 7, 2021
1:30PM to 2:30PM
Date(s) - 07/10/2021
1:30 pm - 2:30 pm
Title: The Phosphinoboration Reaction: TheUndiscovered Country
Date: Thursday, October 7, 2021
Zoom: link available for firstname.lastname@example.org
Host: Nicholas Hoffman (Emslie Group)
Abstract: Over the past few decades, thetransition metal catalysed addition of boron-element (B-E, where E = H, B, Sn,Si, etc) bonds to unsaturated compounds has received a considerable amount ofattention. Given the intensity of interest in the reactivity of B-E bondsit is somewhat surprising that relatively little is known about the analogousaddition chemistry of compounds containing single B-E bonds where E isphosphorus. The corresponding phosphinoboration would introduce a P-C bond anda reactive B-C bond that could be further transformed to provide access to ahost of useful structural motifs and, in this regard, is a worthy target. We have initially reported on the synthesis of phosphinoboronate esters containinga single P-B bond along with the corresponding reactivity studies towards arange of organic substrates including aldehydes, aldimines, alkynes andallenes.1 We report herein recent developments in this area.
1 (a) R. G. Fritzemeier, J. Nekvinda, C.M. Vogels, C. A. Rosenblum, C. Slebodnick, S. A. Westcott and W.L. Santos, Angew.Chem. Int. Ed. 2020, 59, 14358-14362; (b) M. C. Murphy, A.Trofimova, J. H. W. LaFortune, C. M. V. S. J. Geier, J. F. Binder, C. L. B.Macdonald, D. W. Stephan and S. A. Westcott, Dalton Trans. 2020, 49,5092-5099; (c) A. Trofimova, J. H. W. LaFortune, S. A. Westcott and D. W.Stephan, Chem. Commun. 2019, 55, 12100-12103; (d) J. H. W.LaFortune, A. Trofimova, S. A. Westcott and D. W. Stephan, Chem. Eur. J.2019, 25, 12521-12525; (e)J. J. H. W. LaFortune, Z.-W. Qu, K. L.Bamford, A. Trofimova, H. Cummings, S. A. Westcott and D. W. Stephan, Chem.Eur. J. 2019, 25, 12063-12067; (f) S. J. Geier, J. H. W. LaFortune,D. Zhu, S. C. Kosnik, C. L. B. Macdonald, D. W. Stephan and S. A. Westcott, DaltonTrans. 2017, 46, 10876-10885; (g) S. J. Geier, C. M. Vogels, E. N.Daley, A. Decken, N. R. Mellonie, S. Doherty and S. A. Westcott, Chem. Eur.J. 2017, 23, 14485-14499; (h) E. N. Daley, C. M. Vogels, S. J.Geier, A. Decken, S. Doherty and S. A. Westcott, Angew. Chem. Int. Ed.2015, 54, 2121-2125.