Pyridine-Derived N-Heterocyclic Carbenes: An Experimental and Theoretical Evaluation of the Bonding in and Reactivity of Selected Normal and Abnormal Complexes of Nickel(II) and Palladium(II)

Stander‐Grobler, Elzet; Schuster, Oliver; Heydenrych, Greta; Cronje, Stephanie; Tosh, Evangeline; Albrecht, Martin; Frenking, Gernot; Raubenheimer, Helgard G.

doi:10.1021/om100431u

Cited by 70 publications

(43 citation statements)

References 86 publications

(224 reference statements)

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“…Phenyl protons and carbon atoms of these ligands resonate in the same region as previously found for related pyridylidene complexes [15]. Assignments are reported in Section 4.…”

Section: Characterisationsupporting

confidence: 57%

“…The Ni-P and Pd-P bonds are longer than the corresponding bonds in similar imidazol-2-ylidene [18,27] complexes but do not differ significantly from the same bonds in pyridylidene [15] and thiazol-2-ylidene [28] and isoquinolylidene (Pd only) complexes [29]. .…”

Section: Molecular Structures Of 1a 2b and 3bmentioning

confidence: 82%

“…The three palladium compounds 1b, 2b and 3b were used as precatalysts and compared to the three pyridylidene complexes [15] shown in Fig. 6 and Pd(PPh 3 ) 4 .…”

Section: Preliminary Catalytic Resultsmentioning

confidence: 99%

“…Assignments are reported in Section 4. In both the complexes 1a and 1b and their thiazolium precursor I (as well as in unbrominated thiazolium salts [15]) the 13 remarkably low compared to that (d 189.9) of a known a-S carbene complex of iron derived from an isothiazolium salt in which the nitrogen atom is also placed in a remote (but normal) position [16]. The cations of the new ligand precursors I-III are observed in their EI mass spectra.…”

Section: Characterisationmentioning

confidence: 93%

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Normal and abnormal carbene complexes derived from thiazole: Preparation and a preliminary investigation of their relative catalytic performance

et al. 2011

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Readily prepared 2-, 4-and 5-bromo-3-methyl thiazolium triflates react by oxidative substitution with M(PPh 3 ) 4 (M = Ni or Pd) to furnish five of the expected normal and abnormal cationic thiazolylidene complexes (1a, 1b, 2a, 2b, and 3b). Carbene complex formation is accompanied by a ca. 40 ppm downfield shift of the a-N carbene carbons in Pd complexes 1 and 2 in their 13 C NMR spectra but the chemical shift of C(carbene) in the abnormal 3b (d 135.7) is particularly low. Crystal and molecular structures of complexes 1a, 2b, and 3b all indicate a square planar arrangement of the ligands around the central metal atoms. The new complexes catalyse Suzuki-Miyaura aryl coupling.

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“…Phenyl protons and carbon atoms of these ligands resonate in the same region as previously found for related pyridylidene complexes [15]. Assignments are reported in Section 4.…”

Section: Characterisationsupporting

confidence: 57%

Section: Molecular Structures Of 1a 2b and 3bmentioning

confidence: 82%

“…The three palladium compounds 1b, 2b and 3b were used as precatalysts and compared to the three pyridylidene complexes [15] shown in Fig. 6 and Pd(PPh 3 ) 4 .…”

Section: Preliminary Catalytic Resultsmentioning

confidence: 99%

Section: Characterisationmentioning

confidence: 93%

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Normal and abnormal carbene complexes derived from thiazole: Preparation and a preliminary investigation of their relative catalytic performance

et al. 2011

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“…For [31], no additional activation is necessary and attempts to recrystallize [31] from dichloromethane yielded complex [43] (Scheme 19, top). 45 A similar N-alkylation of [31] to give [44] was observed upon reaction of the complex with ethyl bromide (Scheme 19, bottom).…”

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confidence: 99%

Complexes Bearing Protic N-Heterocyclic Carbenes: Synthesis and Applications

Jahnke

Hahn

2014

Chemistry Letters

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Next to complexes bearing N,N′-dialkylazolium-derived N-heterocyclic carbenes (NR,NR-NHCs), the coordination chemistry of protic NHC ligands (NH,NR-NHCs and NH,NH-NHCs) has recently attracted attention. The protic NHC ligands offer multiple opportunities for postsynthetic modifications. This review summarizes methods for the generation of complexes with protic NHC ligands, with a special focus on the recently developed oxidative addition of 2-halogenoazoles to low-valent transition metals. Selected applications for complexes with protic NHC ligands, like the template-controlled preparation of NHC-containing macrocycles and the utilization of the NH function of protic carbene ligands as a molecular recognition unit, will also be discussed.

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Beyond Classical N‐heterocyclic Carbenes II

2017

The Organometallic Chemistry of N‐heterocyclic Carbenes

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Pyridine-Derived N-Heterocyclic Carbenes: An Experimental and Theoretical Evaluation of the Bonding in and Reactivity of Selected Normal and Abnormal Complexes of Nickel(II) and Palladium(II)

Cited by 70 publications

References 86 publications

Normal and abnormal carbene complexes derived from thiazole: Preparation and a preliminary investigation of their relative catalytic performance

Normal and abnormal carbene complexes derived from thiazole: Preparation and a preliminary investigation of their relative catalytic performance

Complexes Bearing Protic N-Heterocyclic Carbenes: Synthesis and Applications

Beyond Classical N‐heterocyclic Carbenes II

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