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Structures, Mechanisms, and Results in Bifunctional Catalysis and Related Species Involving Proton Transfer

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Abstract

Pyridyl- and imidazolylphosphines accelerate anti-Markovnikov alkyne hydration and alkene isomerization and deuteration by factors of 1,000 to more than 10,000. The same features that increase the efficiency of bifunctional catalysts also complicate studies of their mechanism. Evidence for proton transfer and hydrogen bonding in catalytic intermediates comes from computational, mechanistic and structural studies, where 15N NMR data are particularly revealing. Our methods should be useful in other studies of bifunctional catalysis.

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Notes

  1. A footnote in Table 2 of a recent article by the author [39] gives the mistaken impression that the chemical shifts given are relative to formamide δN = 0 ppm when in fact they are relative to formamide δN = −267.8 ppm.

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Acknowledgments

The author would like to thank all of the dedicated co-workers who are co-authors on papers cited; SDSU colleague Professor Andrew Cooksy has been essential to advancing the computational and kinetics portions of this work; Dr. LeRoy Lafferty has assisted the author and his students with NMR experiments; Professor Arnold Rheingold and his group have been invaluable for their X-ray diffraction expertise; and the National Science Foundation has supported not only the work described here (CHE-0415783 and -0719575), but also upgrading the SDSU departmental NMR facility (MRI CHE-0521698).

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  1. Department of Chemistry and Biochemistry, San Diego State University, 5500 Campanile Drive, San Diego, CA, 91282-1030, USA

    Douglas B. Grotjahn

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  1. Douglas B. Grotjahn
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Correspondence to Douglas B. Grotjahn.

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Grotjahn, D.B. Structures, Mechanisms, and Results in Bifunctional Catalysis and Related Species Involving Proton Transfer. Top Catal 53, 1009–1014 (2010). https://doi.org/10.1007/s11244-010-9571-z

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