Synthesis and Reactivity of a Nucleophilic Palladium(II)
Carbene
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Abstract
Two
formal palladium carbene complexes, [PC(sp<sup>2</sup>)P]Pd(PR<sub>3</sub>) (<b>3</b>: R = Me; <b>4</b>: R = Ph) were isolated
and characterized from [PC(sp<sup>3</sup>)H<sub>2</sub>P] ([PC(sp<sup>3</sup>)H<sub>2</sub>P] = bis[2-(di-isopropylphosphino)phenyl]methane, <sup>i</sup>Pr<sub>2</sub>P-C<sub>6</sub>H<sub>4</sub>-CH<sub>2</sub>-C<sub>6</sub>H<sub>4</sub>-P<sup>i</sup>Pr<sub>2</sub>). Structural studies
and DFT calculations indicate that the interaction between palladium
and carbon is best described as a single bond, associated with nucleophilic
character at that carbon atom. The characteristics of <b>3</b> were probed by reactions with electrophiles (MeI), acids (MeOH and
HCl), and <i>para</i>-toluidine
