Mild and rational synthesis of palladium complexes comprising C(4)-bound N-heterocyclic carbenes

Kluser, Evelyne; Neels, Antonia; Albrecht, Martin

doi:10.1039/b611212a

Cited by 63 publications

(35 citation statements)

References 36 publications

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“…Installation of an iodide at the C4 position starting from 4-iodoimidazole 16 has recently been demonstrated to be a useful strategy for preparing the palladium complexes 18 comprising a chelating C4-coordinated carbene ligand (Scheme 12). 38 Variable-temperature analyses indicated that the C4-bonding mode is thermostable up to 100 1C and no rearrangement to thepresumably thermodynamically more stable-C2-bound isomer has been observed. Clearly, oxidative addition to lowvalent metal precursors different from palladium(0) are required to evaluate whether this metallation methodology is of potential general scope.…”

Section: Transmetallationmentioning

confidence: 92%

C4-bound imidazolylidenes: from curiosities to high-impact carbene ligands

2008

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This feature article summarizes the progress achieved thus far in using C4-bound imidazolylidenes as a new class of ligands for transition metals. Since the discovery of this unusual carbene bonding mode in 2001, various rational routes towards complexes containing C4-bound carbenes have evolved. These advances allowed for studying the impact of this new type of ligand on the transition metal center, both from a fundamental point of view as well as from a more applied perspective, in particular for catalytic applications. The promising results accomplished in this relatively short period of time demonstrate the potential of C4-bound imidazolylidenes as unique carbene ligands for inducing catalytic activity and for mediating unprecedented transformations.

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Section: Transmetallationmentioning

confidence: 92%

C4-bound imidazolylidenes: from curiosities to high-impact carbene ligands

2008

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“…Oxidative addition to palladium(0) affords complex 3 comprising a chelating C(4)-bound imidazolylidene ligand (Scheme 3). [18] Variable temperature analysis has shown that the abnormal bonding mode is thermally stable at least up to 100 °C. No rearrangement to the presumably thermodynamically more stable C(2)-bound isomer has been detected.…”

Section: Metallation Via Activation Of the Imidazolium C(4) Positionmentioning

confidence: 99%

Abnormal Carbenes as Ligands in Transition Metal Chemistry: Curiosities with Exciting Perspectives

Albrecht¹

2009

Chimia

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This review compiles the advances achieved in our laboratories using abnormal and less heteroatomstabilized carbenes as ligands for transition metal chemistry. Fundamental studies allowed the evaluation of the impact of this new class of ligands both electronically and sterically. Based on these results, initial catalytic applications have been devised in the area of H-H and C-H bond activation, demonstrating the potential of abnormal carbenes as unique ligands for transition metals.

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“…[1][2][3][4][5] Only recently it has been shown that an abnormal binding mode via the C4 (or C5) position of imidazolylidenes yields extraordinary electron rich metal centers. [6][7][8][9][10][11][12][13][14][15][16][17] These discoveries led to a considerably increased interest in "non-classical" NHCs, i.e. carbenes that are not stabilized by two adjacent heteroatoms.…”

Section: Introductionmentioning

confidence: 99%