Organometallics
Article
and Electronic Modifications. J. Am. Chem. Soc. 2003, 125 (41),
CN CH COCH CNBu, CR SH und SR− (R = Et, Ph, o-
−
−
−
−
3 3 2
1
(
2502−12508.
C H NH ). J. Organomet. Chem. 1997, 541 (1−2), 291−305.
6
4
2
14) Waltman, A. W.; Grubbs, R. H. A New Class of Chelating N-
(31) Downing, S. P.; Danopoulos, A. A. Indenyl- and Fluorenyl-
Functionalized N-Heterocyclic Carbene Complexes of Titanium and
Vanadium. Organometallics 2006, 25 (6), 1337−1340.
Heterocyclic Carbene Ligands and Their Complexes with Palladium.
Organometallics 2004, 23 (13), 3105−3107.
(
Heterocylic Carbenes Involving Heterocycle Cleavage. Organo-
metallics 2006, 25 (18), 4238−4239.
(
15) Waltman, A. W.; Ritter, T.; Grubbs, R. H. Rearrangement of N-
(32) Sun, H.-M.; Hu, D.-M.; Wang, Y.-S.; Shen, Q.; Zhang, Y.
Synthesis and Characterization of Indenyl-Functionalized N-Hetero-
cyclic Carbene Complex of Ni(II). J. Organomet. Chem. 2007, 692
(
4), 903−907.
33) Liddle, S. T.; Edworthy, I. S.; Arnold, P. L. Anionic Tethered
N-Heterocyclic Carbene Chemistry. Chem. Soc. Rev. 2007, 36 (11),
732−1744.
34) Pape, F.; Teichert, J. F. Dealing at Arm’s Length: Catalysis with
16) Wang, Z.-G.; Sun, H.-M.; Yao, H.-S.; Yao, Y.-M.; Shen, Q.;
(
Zhang, Y. Bis-Aryloxo-Functionalized NHC Complexes of Ytterbium-
(
(
6
III): Syntheses and Structures of Yb[O-4,6-tBu -C H -2-CH {C-
RNCHCHN)}] N(iPr) (R = iPr, Me). J. Organomet. Chem. 2006,
91 (15), 3383−3390.
2 6 2 2
1
2
2
(
N-Heterocyclic Carbene Ligands Bearing Anionic Tethers: Dealing at
Arm’s Length: Catalysis with N-Heterocyclic Carbene Ligands
Bearing Anionic Tethers. Eur. J. Org. Chem. 2017, 2017 (29),
(
17) Wang, Z.-G.; Sun, H.-M.; Yao, H.-S.; Shen, Q.; Zhang, Y.
Mono- and Tris-Phenoxo-Tethered N-Heterocyclic Carbene Yttrium
Complexes: Syntheses and Molecular Structures. Organometallics
2
4
(
206−4229.
35) Khusnutdinova, J. R.; Milstein, D. Metal-Ligand Cooperation.
Angew. Chem., Int. Ed. 2015, 54 (42), 12236−12273.
36) Braunstein, P. Functional ligands and complexes for new
006, 25 (19), 4436−4438.
18) Zhang, D.; Kawaguchi, H. Deprotonation Attempts on
(
Imidazolium Salt Tethered by Substituted Phenol and Construction
of Its Magnesium Complex by Transmetalation. Organometallics
2
(
(
structures, homogeneous catalysts and nanomaterials. J. Organomet.
Chem. 2004, 689 (24), 3953−3967.
006, 25 (22), 5506−5509.
19) Li, W.; Sun, H.; Chen, M.; Wang, Z.; Hu, D.; Shen, Q.; Zhang,
(37) Powers, I. G.; Uyeda, C. Metal−Metal Bonds in Catalysis. ACS
Y. Synthesis of Salicylaldiminato-Functionalized N-Heterocyclic
Carbene Complex of Nickel(II) and Its Catalytic Activity for Styrene
Polymerization. Organometallics 2005, 24 (24), 5925−5928.
Catal. 2017, 7 (2), 936−958.
38) Peris, E. Smart N-Heterocyclic Carbene Ligands in Catalysis.
Chem. Rev. 2018, 118 (19), 9988−10031.
39) Legault, C. Y.; Kendall, C.; Charette, A. B. Structure and
(
(
20) Aihara, H.; Matsuo, T.; Kawaguchi, H. Titanium N-
(
Heterocyclic Carbene Complexes Incorporating an Imidazolium-
Linked Bis(Phenol). Chem. Commun. 2003, No. 17, 2204−2205.
(
Reactivity of a New Anionic N-Heterocyclic Carbene Silver(I)
Complex. Chem. Commun. 2005, No. 30, 3826−38.
21) Zhang, D.; Aihara, H.; Watanabe, T.; Matsuo, T.; Kawaguchi,
(40) Guernon, H.; Legault, C. Y. N-Acyliminoimidazolium Ylides as
H. Zirconium complexes of the tridentate bis(aryloxide)-N-hetero-
cyclic-carbene ligand: Chloride and alkyl functionalized derivatives. J.
Organomet. Chem. 2007, 692 (1−3), 234−242.
Precursors to Anionic N -Heterocyclic Carbene Ligands: Control of
Topology and Reactivity. Organometallics 2013, 32 (6), 1988−1994.
(
41) Elguero, J.; Goya, P.; Rozas, I.; Catalan, J.; De Paz, J. L. G. An
́
(
22) (a) Ketz, B. E.; Ottenwaelder, X. G.; Waymouth, R. M.
AB Initio Comparative Study of the Electronic Properties of
Synthesis, Structure, and Olefin Polymerization with Nickel(II) N-
Heterocyclic Carbene Enolates. Chem. Commun. 2005, No. 45, 5693−
5
Reactivity of an Allylpalladium N-Heterocyclic Carbene Enolate
Complex. Organometallics 2004, 23 (12), 2835−2837.
(
Sulfonamides and Amides. J. Mol. Struct.: THEOCHEM 1989, 184
(
1−2), 115−129.
695. (b) Ketz, B. E.; Cole, A. P.; Waymouth, R. M. Structure and
(
42) Legault, C.; Charette, A. B. Highly Efficient Synthesis of O-
(2,4-Dinitrophenyl)Hydroxylamine. Application to the Synthesis of
Substituted N-Benzoyliminopyridinium Ylides. J. Org. Chem. 2003, 68
(18), 7119−7122.
(43) For the X-ray diffraction analysis of complex 10f, see the
Supporting Information.
(44) Ellul, C. E.; Reed, G.; Mahon, M. F.; Pascu, S. I.; Whittlesey, M.
K. Tripodal N-Heterocyclic Carbene Complexes of Palladium and
Copper: Syntheses, Characterization, and Catalytic Activity. Organo-
metallics 2010, 29 (18), 4097−4104.
23) Arnold, P. L.; Mungur, S. A.; Blake, A. J.; Wilson, C. Anionic
Amido N-Heterocyclic Carbenes: Synthesis of Covalently Tethered
Lanthanide−Carbene Complexes. Angew. Chem., Int. Ed. 2003, 42
(
48), 5981−5984.
(
24) Liddle, S. T.; Arnold, P. L. Synthesis of Heteroleptic
Cerium(III) Anionic Amido-Tethered N-Heterocyclic Carbene
Complexes. Organometallics 2005, 24 (11), 2597−2605.
(
Lanthanide-Bound N-Heterocyclic Carbenes. Chem. Commun. 2005,
No. 45, 5638−5640.
(
25) Arnold, P. L.; Liddle, S. T. Regioselective C−H Activation of
(45) Oeschger, R. J.; Chen, P. Structure and Gas-Phase
Thermochemistry of a Pd/Cu Complex: Studies on a Model for
Transmetalation Transition States. J. Am. Chem. Soc. 2017, 139 (3),
1069−1072.
26) Mungur, S. A.; Blake, A. J.; Wilson, C.; McMaster, J.; Arnold, P.
(46) Bader, R. F. W. Atoms in Molecules: A Quantum Theory; Oxford
L. Titanium(IV) Alkoxy-N-Heterocyclic Carbenes: Structural Prefer-
ences of Alkoxide and Bromide Adducts. Organometallics 2006, 25
University Press: Oxford, U. K., 1990.
(
8), 1861−1867.
(
27) Spencer, L. P.; Winston, S.; Fryzuk, M. D. Tridentate Amido
Carbene Ligands in Early-Transition-Metal Coordination Chemistry.
Organometallics 2004, 23 (14), 3372−3374.
(
28) Spencer, L. P.; Fryzuk, M. D. Synthesis and Reactivity of
Zirconium and Hafnium Complexes Incorporating Chelating
Diamido-N-Heterocyclic-Carbene Ligands. J. Organomet. Chem.
2
(
005, 690 (24−25), 5788−5803.
29) Spencer, L. P.; Beddie, C.; Hall, M. B.; Fryzuk, M. D. Synthesis,
Reactivity, and DFT Studies of Tantalum Complexes Incorporating
Diamido-N-Heterocyclic Carbene Ligands. Facile Endocyclic C−H
Bond Activation. J. Am. Chem. Soc. 2006, 128 (38), 12531−12543.
(
30) Sellmann, D.; Allmann, C.; Heinemann, F.; Knoch, F.; Sutter, J.
̈
Ubergangsmetallkomplexe mit Schwefelliganden CXXIV. Koordina-
tion von C- und S-Liganden an MetallCarbenThiolat-Fragmente
II
II II
2−
[
M(‘S C’)] [M = Ni Pd Pt ‘S C’ = 1,3-Imidazolidinyl-NN′-bis(2-
2
2
benzolthiolat)(2 − )]. [M(L)(‘S C’)]-Komplexe mit L =
2
H
Organometallics XXXX, XXX, XXX−XXX