A Radical Mechanism for Frustrated Lewis Pair Reactivity

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Presentation transcript:

A Radical Mechanism for Frustrated Lewis Pair Reactivity Liu (Leo) Liu, Levy L. Cao, Yue Shao, Gabriel Ménard, Douglas W. Stephan Chem Volume 3, Issue 2, Pages 259-267 (August 2017) DOI: 10.1016/j.chempr.2017.05.022 Copyright © 2017 Elsevier Inc. Terms and Conditions

Chem 2017 3, 259-267DOI: (10.1016/j.chempr.2017.05.022) Copyright © 2017 Elsevier Inc. Terms and Conditions

Figure 1 Plausible Mechanisms of Small-Molecule Activation by FLPs (A) Mechanism of activation of generic substrate (X2) by FLPs via an “encounter complex.” (B) Proposed mechanism of activation of generic substrate by FLPs via the SET process. Chem 2017 3, 259-267DOI: (10.1016/j.chempr.2017.05.022) Copyright © 2017 Elsevier Inc. Terms and Conditions

Figure 2 Reactivity of tBu3P/E(C6F5)3 toward pO2C6Cl4 and Ph3SnH Reactions of tBu3P, E(C6F5)3 (E = B or Al) with p-O2C6Cl4 and Ph3SnH (see also Figures S1–S19). POV-ray depictions of the molecular structures of 1 and 4 are shown (see also Table S1). Colors are as follows: C, black; F, pink; B, yellow-green; Al, light blue; O, red; Sn, green-blue; P, orange; Cl, aquamarine; H, gray. All hydrogen atoms except the bridging hydride of the anion of 4 are omitted for clarity. Chem 2017 3, 259-267DOI: (10.1016/j.chempr.2017.05.022) Copyright © 2017 Elsevier Inc. Terms and Conditions

Figure 3 Reactivity of Mes3P/E(C6F5)3 toward pO2C6Cl4 and Ph3SnH Reactions of Mes3P and E(C6F5)3 (E = B or Al) with pO2C6Cl4 and Ph3SnH (see also Figures S20–S46). Insert: picture of a solution of Mes3P and Al(C6F5)3 in chlorobenzene and the experimental and simulated X-band EPR spectra derived from the Mes3P/Al(C6F5)3 solution (observed, black; simulated, red); POV-ray depictions of the molecular structures of 7 and 8 are shown (see also Table S1). Colors are as follows: C, black; F, pink; B, yellow-green; Cl, aquamarine; P, orange; O, red; H, gray. All hydrogen atoms except the phosphonium proton of 7 are omitted for clarity. Chem 2017 3, 259-267DOI: (10.1016/j.chempr.2017.05.022) Copyright © 2017 Elsevier Inc. Terms and Conditions