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Noninnocent Behavior of PCP and PCN Pincer Ligands of Late Metal Complexes

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Book cover Organometallic Pincer Chemistry

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 40))

Abstract

Pincer complexes are generally viewed as stable compounds in which the pincer ligand framework remains unchanged during stoichiometric and catalytic reactions. However, there are now several cases in which the pincer ligand itself undergoes transformations that result in extraordinary reactivity of the metal complex and formation of unusual species. In the current chapter, we review our work on “noninnocent” reactivity modes of various PCP and PCN-type pincer ligands of Rh, Ir, Ru, Os, Pd, and Pt. Participation of the arene ring in the reactivity of PCP type complexes has led to formation of unprecedented quinonoid complexes, including complexes in which the pincer ligand adopts structures of quinone methides, thio-quinone methides, xylylenes, methylene arenium, and oxo-arenium compounds. In addition, pincer systems can collapse and be regenerated under redox conditions, and reduction can lead to a ring-localized radical anion complex. The generation of C–H agostic arene PCP complexes has led to new insights regarding the C–H bond activation process, and the effect of CO ligands on it.

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Notes

  1. 1.

    We are aware of two examples of completely nonplanar (rather than distorted square planar) Pd(II)L4 complexes, only one of them being diamagnetic [112, 113].

  2. 2.

    A mechanism involving organic halide oxidative addition to generate dibenzyl or biphenyl is also possible. See, for example [114].

  3. 3.

    In analogy to nonchelating systems, where reduction of PtCl2L2 (L = bulky tert-phosphines) with Na/Hg in THF affords PtL2 complexes, while reduction of PdCl2L2 (L = bulky tert-phosphines) with Na/Hg in THF resulted in formation of metallic palladium. The reduction was achieved only when excess phosphine was used. See [116] and references therein.

  4. 4.

    For nonisolated, anionic palladium(0) intermediates, and their involvement in oxidative addition reactions, see [119, 120].

  5. 5.

    Very unstable, not isolated [144].

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  1. Department of Organic Chemistry, The Weizmann Institute of Science, 76100, Rehovot, Israel

    Elena Poverenov & David Milstein

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  1. Elena Poverenov
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  1. Debye Research Institute, Department of Metal-Mediated Synthesis, Utrecht University, Padualaan 8, Utrecht, 3584, Netherlands

    Gerard van Koten

  2. The Kimmel Center for Molecular Design, Department of Organic Chemistry, The Weizmann Institute of Science, no street, Rehovot, 76100, Israel

    David Milstein

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Poverenov, E., Milstein, D. (2013). Noninnocent Behavior of PCP and PCN Pincer Ligands of Late Metal Complexes. In: van Koten, G., Milstein, D. (eds) Organometallic Pincer Chemistry. Topics in Organometallic Chemistry, vol 40. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-31081-2_2

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