DOI: 10.1021/om701151g. Computational Studies of Intramolecular Carbon−Heteroatom Bond Activation of N-Aryl Heterocyclic Carbene Ligands

Computational Studies of Intramolecular Carbon−Heteroatom Bond Activation of N-Aryl Heterocyclic Carbene Ligands

10.1021/om701151g

Crossref journal-article

American Chemical Society (ACS)

Organometallics (316)

Bibliography

Diggle, R. A., Kennedy, A. A., Macgregor, S. A., & Whittlesey, M. K. (2008). Computational Studies of Intramolecular CarbonâHeteroatom Bond Activation of N-Aryl Heterocyclic Carbene Ligands. Organometallics, 27(5), 938â944.

Authors 4

Richard A. Diggle (first)
Andrew A. Kennedy (additional)
Stuart A. Macgregor (additional)
Michael K. Whittlesey (additional)

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With ano-tolyl substituent as in4-CH3C(aryl)−H activation will also be favored by the formation of a five-membered ring. This factor can also reverse the preference in favor of C(sp3)−H activation, as seen in the reactions of 1-benzyl-3-tert-butylimidazol-2-ylidene at Ir. The observation of C(aryl)−H activation with the 1-benzyl-3-isopropylimidazol-2-ylidene analogue, however, indicates how subtle these competition effects can be, and in this case the variable reactivity was ascribed to steric effects. See ref 15e.
Alternative forms of4a′-OHand4a′-NH2without a direct Ru−N or Ru−O interaction could also be located. The alternative form of4a′-NH2featured an Ru···H−N agostic interaction (E= +2.6 kcal/mol), while for4a′-OHa species with a more open P1−Ru−C3angle of 136° and a longer Ru···O2 distance of 3.77 Å was seen (E= +1.6 kcal/mol). In all cases, however, the most stable structures of4a′-Xare shown in Figure 1.
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Dates

Type	When
Created	17 years, 6 months ago (Feb. 14, 2008, 1:01 a.m.)
Deposited	2 years, 5 months ago (March 16, 2023, 4:28 a.m.)
Indexed	6 months, 2 weeks ago (Feb. 21, 2025, 2:07 a.m.)
Issued	17 years, 6 months ago (Feb. 14, 2008)
Published	17 years, 6 months ago (Feb. 14, 2008)
Published Online	17 years, 6 months ago (Feb. 14, 2008)
Published Print	17 years, 6 months ago (March 1, 2008)

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BibTeX

@article{Diggle_2008, title={Computational Studies of Intramolecular Carbon−Heteroatom Bond Activation of N-Aryl Heterocyclic Carbene Ligands}, volume={27}, ISSN={1520-6041}, url={http://dx.doi.org/10.1021/om701151g}, DOI={10.1021/om701151g}, number={5}, journal={Organometallics}, publisher={American Chemical Society (ACS)}, author={Diggle, Richard A. and Kennedy, Andrew A. and Macgregor, Stuart A. and Whittlesey, Michael K.}, year={2008}, month=feb, pages={938–944} }

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