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Journal articles on the topic 'Zerovalent metal complexes'

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Published: 4 June 2021

Last updated: 7 February 2022

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1

Cavell, Ronald G., and Ian G. Phillips. "Reactions of Cyclopolyphosphines with Zerovalent Platinum Group Metal Complexes." Phosphorous and Sulfur and the Related Elements 30, no. 1-2 (March 1987): 117–20. http://dx.doi.org/10.1080/03086648708080536.

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2

Bennett, Martin A. "Aryne Complexes of Zerovalent Metals of the Nickel Triad." Australian Journal of Chemistry 63, no. 7 (2010): 1066. http://dx.doi.org/10.1071/ch10198.

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The chemistry of dihapto-aryne complexes of the zerovalent Group 10 metals of general formula [M(η2-aryne)L2] (M = Ni, Pd, Pt; L = various tertiary phosphines) is reviewed, with emphasis on the highly reactive nickel(0) compounds (aryne = benzyne, C6H4; 4,5-difluorobenzyne, 4,5-C6H2F2; 2,3-naphthalyne, 2,3-C10H6; L2 = 2 PEt3, 2 PiPr3, 2 PCy3, dcpe). These can be generated by alkali metal reduction of the appropriate (2-halogenoaryl)nickel(ii) halide precursors, such as [NiX(2-XC6H4)L2], which in turn are accessible by oxidative addition of the 1,2-dihaloarene to nickel(0) precursors such as [Ni(1,5-COD)2]. The X-ray structure of [Ni(η2-C6H4)(dcpe)] shows that this compound is a typical 16-electron Ni(0) (3d10) species in which benzyne acts as a 2π-electron donor. Several unusual organonickel compounds derived from [Ni(η2-4,5-C6H2F2)(PEt3)2] have been isolated recently, including [Ni2(μ-η2:η2-4,5-C6H2F2)(PEt3)4], in which a 4π-electron donor 4,5-difluorobenzyne is located at right-angles to a pair of nickel atoms. Free benzyne can be intercepted by both [Ni(η2-C2H4)(dcpe)] and [Pt(η2-C2H4)(PPh3)2], but the resulting benzyne complexes rapidly insert benzyne to give the appropriate η1:η1-2,2′-biphenylyl complexes. [Pt(η2-C6H4)(PPh3)2] also undergoes rapid ortho-metallation to give [PtPh(2-C6H4PPh2)(PPh3)]. However, a trapping reaction has been used to make the first 1,4-benzdiyne complex, [{Ni(dcpe)2}2(μ-η2:η2-1,4-C6H2)] by treatment of the 4-fluorobenzyne complex [Ni(η2-4-FC6H3)(dcpe)] with LiTMP. The use of alkali metals in the preparation of the η2-benzyne complexes is avoided in a more recently developed procedure, which starts from (2-bromophenyl)boronic acid, and is based on Suzuki–Miyaura coupling. This procedure has made accessible for the first time an aryne complex of palladium(0), [Pd(η2-C6H4)(PCy3)2], and the labile nickel(0) complex [Ni(η2-C6H4)(PPh3)2]. The aryne-nickel(0) complexes Ni(η2-aryne)L2 (L2 = 2 PEt3, dcpe) undergo sequential insertions into the aryne-metal bond with unsaturated molecules, such as CO, C2F4, substituted alkynes, substituted diynes, alkynylphosphines, and alkynyl thioethers, often with considerable regioselectivity. After the reductive elimination of two nickel-carbon σ-bonds, a variety of interesting polycyclic compounds can be obtained.

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3

Braunschweig, Holger, Rian D. Dewhurst, Florian Hupp, Christina Kaufmann, Ashwini K. Phukan, Christoph Schneider, and Qing Ye. "Gauging metal Lewis basicity of zerovalent iron complexes via metal-only Lewis pairs." Chemical Science 5, no. 10 (July 15, 2014): 4099. http://dx.doi.org/10.1039/c4sc01539h.

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4

Braunschweig, Holger, Carina Brunecker, Rian D. Dewhurst, and Christoph Schneider. "Does Lewis basicity correlate with catalytic performance in zerovalent group 8 complexes?" Zeitschrift für Naturforschung B 73, no. 3-4 (April 25, 2018): 149–53. http://dx.doi.org/10.1515/znb-2017-0193.

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AbstractA set of 18 zerovalent group 8 metal complexes of the form [MLn(CO)5−n] (M=Fe, Ru, Os; L=neutral donor;n=0–2) were screened for their catalytic performance in aldehyde hydrosilylation and olefin hydroboration reactions. Although none of the untested catalysts were found to perform better than the previously-published complex [Fe(CO)4(IMes)] (IMes=1,3-Dimesityliidazol-2-ylidene), the results suggest that the Lewis basicity of the metal complex does not play a critical role in the catalysis of these two reactions.

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5

Stufkens, Derk J. "Spectroscopy, photophysics and photochemistry of zerovalent transition metal α-diimine complexes." Coordination Chemistry Reviews 104, no. 1 (July 1990): 39–112. http://dx.doi.org/10.1016/0010-8545(90)80040-z.

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6

Choi, Henry W., and E. L. Muetterties. "Zerovalent metal phosphite complexes. Synthesis of RE2 [P (OCH3)3]10." Bulletin des Sociétés Chimiques Belges 89, no. 10 (September 1, 2010): 809–11. http://dx.doi.org/10.1002/bscb.19800891005.

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7

Branzan, Ramona M. C., Jutta Kösters, Mareike C. Jahnke, and F. Ekkehardt Hahn. "Oxidative addition of N-ether-functionalized 2-chlorobenzimidazole to d10 metals." Zeitschrift für Naturforschung B 71, no. 10 (October 1, 2016): 1077–85. http://dx.doi.org/10.1515/znb-2016-0137.

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AbstractReaction of 2-chloro-N-(methoxymethyl)benzimidazole 1 with zerovalent group 10 metal complexes in the presence of an additional proton source yielded, via an oxidative addition of the C2–Cl bond, complexes with a protic NH,NR-substituted (R=methoxymethyl) benzimidazolin-2-ylidene ligand. The oxidative addition of 1 to Ni0 and Pd0 complexes proceeded with the exclusive formation of the trans-configured complexes trans-[2]BF4 and trans-[3]BF4, respectively. Contrary to this observation, the reaction of 1 with a more substitution inert Pt0 complex leads, depending on the reaction temperature, to a mixture of cis-/trans-[4]BF4 or exclusively to trans-[4]BF4. The molecular structures of all three trans-configured complexes were determined.

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8

Manuta, David M., and Alistair J. Lees. "Solvatochromism of the metal to ligand charge-transfer transitions of zerovalent tungsten carbonyl complexes." Inorganic Chemistry 25, no. 18 (August 1986): 3212–18. http://dx.doi.org/10.1021/ic00238a025.

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9

Belotti, Diana, Florian Kampert, Mareike C. Jahnke, and F. Ekkehardt Hahn. "Oxidative addition of a 8-bromotheobromine derivative to d 10 metals." Zeitschrift für Naturforschung B 76, no. 3-4 (March 4, 2021): 227–35. http://dx.doi.org/10.1515/znb-2021-0011.

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Abstract Reaction of 8-bromo-7-ethyl-3-methylxanthine 1 with zerovalent group 10 metal complexes gave via an oxidative addition of the C–Br bond the neutral complexes trans-[2] (M = Pd) and trans-[3] (M = Pt) bearing a theobromine-derived azolato ligand. While the oxidative addition to [Pd0(PPh3)4] gave exclusively trans-[2], the reaction with the more substitution-inert [Pt0(PPh3)4] yielded after 1 day the kinetic product cis-[3], which was converted under heating for a total of 3 days completely into the thermodynamically more stable complex trans-[3]. Treatment of trans-[2], trans-[3] or the mixture of cis-/trans-[3] with the proton source HBF4⋅Et2O led to complexes trans-[4]BF4, trans-[5]BF4 and a mixture of cis/trans-[5]BF4 with retention of the original ratio of cis to trans, respectively. The molecular structures of the azolato complexes trans-[2] and trans-[3] and of the theobromine derived pNHC complexes trans-[4]BF4 and trans-[5]BF4 have been determined by X-ray diffraction studies.

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10

Pacchioni, Gianfranco, and Paul S. Bagus. "Metal-phosphine bonding revisited. .sigma.-Basicity, .pi.-acidity, and the role of phosphorus d orbitals in zerovalent metal-phospine complexes." Inorganic Chemistry 31, no. 21 (October 1992): 4391–98. http://dx.doi.org/10.1021/ic00047a029.

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11

Darensbourg, Donald J., Kathryn M. Sanchez, Joseph H. Reibenspies, and Arnold L. Rheingold. "Synthesis, structure, and reactivity of zerovalent group 6 metal pentacarbonyl aryl oxide complexes. Reactions with carbon dioxide." Journal of the American Chemical Society 111, no. 18 (August 1989): 7094–103. http://dx.doi.org/10.1021/ja00200a031.

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12

Cooper, Alasdair K., Paul M. Burton, and David J. Nelson. "Nickel versus Palladium in Cross-Coupling Catalysis: On the Role of Substrate Coordination to Zerovalent Metal Complexes." Synthesis 52, no. 04 (December 19, 2019): 565–73. http://dx.doi.org/10.1055/s-0039-1690045.

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A detailed comparison of the effect of coordinating functional groups on the performance of Suzuki–Miyaura reactions catalysed by nickel and palladium is reported, using competition experiments, robustness screening, and density functional theory calculations. Nickel can interact with a variety of functional groups, which manifests as selectivity in competitive cross-coupling reactions. The presence of these functional groups on exogenous additives has effects on cross-coupling reactions that range from a slight improvement in yield to the complete cessation of the reaction. In contrast, palladium does not interact sufficiently strongly with these functional groups to induce selectivity in cross-coupling reactions; the selectivity of palladium-catalysed cross-coupling reactions is predominantly governed by aryl halide electronic properties.

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13

Barybin, Mikhail V., Victor G. Young, and John E. Ellis. "First Paramagnetic Zerovalent Transition Metal Isocyanides. Syntheses, Structural Characterizations, and Magnetic Properties of Novel Low-Valent Isocyanide Complexes of Vanadium1." Journal of the American Chemical Society 122, no. 19 (May 2000): 4678–91. http://dx.doi.org/10.1021/ja000212w.

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14

Bennett, Martin A., Mark Bown, and David C. R. Hockless. "Tris(dimethylphenylphosphine)ruthenium(0) Complexes of n4-Coordinated Polycyclic Aromatic Hydrocarbons." Australian Journal of Chemistry 53, no. 6 (2000): 507. http://dx.doi.org/10.1071/ch00068.

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From the reaction of [Ru2Cl3(PMe2Ph)6] Cl with the appropriate radical anions, yellow complexes of general formula [Ru(PMe2Ph)3(η4-arene)] [arene = naphthalene (C10H8) (1), anthracene (C14H10) (2), and triphenylene (C18H12) (3)] have been isolated in poor yield and characterized by elemental analysis, n.m.r. (1H, 13C, 31P) spectroscopy and single-crystal X-ray diffraction. Crystal data: (1), monoclinic, C2/c, a 31.096(8), b 12.012(4), c 17.078(8) Å, β 104.41(3)˚, V 6178(4) Å3, ? 8, refined to final R value of 0.032 with use of 3641 reflections [I > 3σ(I)]; (2), monoclinic, C2/c, a 55.909(4), b 14.348(5), c 17.573(5) Å, β 105.41(1)˚, V 13590(6) Å3, Z 16 (two molecules per asymmetric unit), refined to final R value of 0.049 with use of 7770 reflections [I > 3σ(I)]; (3), mono-clinic, Pn, a 9.377(3), b 12.229(3), c 15.975(3) Å, β 103.51(2)˚, V 1781.2 (7) Å3, Z 2, refined to final R value of 0.026 with use of 2830 reflections [I > 3σ(I)]. In each case, coordination of the zerovalent metal fragment Ru(PMe2Ph)3 to the diene section of one of the terminal rings causes the aromatic molecule to be folded by c. 40˚ at the outer carbon atoms of the diene. The coordination geometry about ruthenium is approximately square pyramidal, with the diene and two tertiary phosphines in the equatorial plane and the remaining tertiary phosphine in the axial site.

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15

Fischer, Paul J., Victor G. Young, Jr., and John E. Ellis. "[Ti(CO)4(η3-BH4)]− and [Ti(CO)4(η5-C4H4N)]−: The First Zerovalent Metal Complexes Containingη3-Borohydride and Pyrrolyl Ligands." Angewandte Chemie International Edition 39, no. 1 (January 3, 2000): 189–91. http://dx.doi.org/10.1002/(sici)1521-3773(20000103)39:1<189::aid-anie189>3.0.co;2-o.

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16

Fischer, Paul J., Victor G. Young, Jr., and John E. Ellis. "[Ti(CO)4(η3-BH4)]− and [Ti(CO)4(η5-C4H4N)]−: The First Zerovalent Metal Complexes Containing η3-Borohydride and Pyrrolyl Ligands." Angewandte Chemie 112, no. 1 (January 3, 2000): 195–97. http://dx.doi.org/10.1002/(sici)1521-3757(20000103)112:1<195::aid-ange195>3.0.co;2-j.

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17

Makhankova, V. G., O. Yu Vassilyeva, V. N. Kokozay, and B. W. Skelton. "Zerovalent copper in reactions with triethanolamine and cobalt(II) salts: syntheses, structural, spectroscopic and magnetic studies of novel mixed-metal Cu/Co complexes." Acta Crystallographica Section A Foundations of Crystallography 56, s1 (August 25, 2000): s339. http://dx.doi.org/10.1107/s0108767300027136.

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18

Vinogradova, Elena A., Olga Yu. Vassilyeva, Volodymyr N. Kokozay, Philip J. Squattrito, Jan Reedijk, Gerard A. Van Albada, Wolfgang Linert, Satish K. Tiwary, and Paul R. Raithby. "Symmetric and asymmetric trinuclear cores in novel μ-alkoxo-bridged mixed-metal CuII2ZnII complexes: synthesis from zerovalent copper and zinc oxide, structure and magnetism." New Journal of Chemistry 25, no. 7 (2001): 949–53. http://dx.doi.org/10.1039/b101883n.

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19

Brennessel, William W., Alexander Romanenkov, Victor G. Young, and John E. Ellis. "Tantalum isocyanide complexes: TaI(CNDipp)6 (Dipp is 2,6-diisopropylphenyl) and ionic [Ta(CNDipp)7][Ta(CNDipp)6], a formal disproportionation product of the 17-electron Ta0 metalloradical Ta(CNDipp)6." Acta Crystallographica Section C Structural Chemistry 75, no. 2 (January 23, 2019): 135–40. http://dx.doi.org/10.1107/s2053229619000834.

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Treatment of tetraethylammonium hexacarbonyltantalate, [Et4N][Ta(CO)6], with 1.1 equivalents of molecular iodine (I2) in tetrahydrofuran (THF) at 200 K, followed by the addition of 6.0 equivalents of 2,6-diisopropylphenyl isocyanide (CNDipp) and slow warming to 293 K over a 24 h period gave the tantalum(I) iodide derivative hexakis(2,6-diisopropylphenyl isocyanide-κC)iodidotantalum(I), [TaI(C13H17N)6] or TaI(CNDipp)6, 1. Recrystallization of this substance from pentane provided deep-red nearly black parallelepipeds of the product, which was characterized by single-crystal X-ray diffraction. Addition of 1 in THF at 200 K to a suspension of an excess (5.8 equivalents) of caesium graphite (CsC8), followed by warming, filtration, and solvent removal, afforded a dark-green oily solid of unknown composition, from which several red–brown rhombohedral plates of the ditantalum salt heptakis(2,6-diisopropylphenyl isocyanide-κC)tantalum hexakis(2,6-diisopropylphenyl isocyanide-κC)tantalate, [Ta(C13H17N)7][Ta(C13H17N)6] or [Ta(CNDipp)7][Ta(CNDipp)6], 2, were harvested. Salt 2 is a unique substance, as it is the only known example of a salt containing a homoleptic cation, [MLx ]+, and a homoleptic anion, [MLy ]−, with the same transition metal and π-acceptor ligand L. In solution, 2 undergoes full comproportionation to afford the recently reported 17-electron paramagnetic zerovalent tantalum complex Ta(CNDipp)6, the only known isolable TaL 6 complex of Ta0.

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20

Phillips, Ian G., Richard G. Ball, and Ronald G. Cavell. "Reactions of perfluoromethyl-substituted cyclopolyphosphines with zerovalent group 10 metal complexes. Crystal and molecular structure of a [palladium] complex with a coordinated diphosphene, [Pd(.eta.2-CF3P:PCF3)(PPh3)2]." Inorganic Chemistry 31, no. 9 (April 1992): 1633–41. http://dx.doi.org/10.1021/ic00035a022.

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21

King, Wayne A., Santo Di Bella, Giuseppe Lanza, Karl Khan, David J. Duncalf, F. Geoffrey N. Cloke, Ignazio L. Fragala, and Tobin J. Marks. "Metal−Ligand Bonding and Bonding Energetics in Zerovalent Lanthanide, Group 3, Group 4, and Group 6 Bis(arene) Sandwich Complexes. A Combined Solution Thermochemical and ab Initio Quantum Chemical Investigation." Journal of the American Chemical Society 118, no. 3 (January 1996): 627–35. http://dx.doi.org/10.1021/ja9529697.

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22

PHILLIPS, I. G., R. G. BALL, and R. G. CAVELL. "ChemInform Abstract: Reactions of Perfluoromethyl-Substituted Cyclopolyphosphines with Zerovalent Group 10 Metal Complexes. Crystal and Molecular Structure of a Complex with a Coordinated Diphosphene, (Pd(η2-CF3P=PCF3)( PPh3)2)." ChemInform 23, no. 33 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199233257.

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23

Fischer, Paul J., Shuruthi Senthil, Jeremy T. Stephan, McKinley L. Swift, Meghan D. Storlie, Emily T. Chan, Matthew V. Vollmer, and Victor G. Young. "Inductive modulation of tris(phosphinomethyl)phenylborate donation at group VI metals via borate phenyl substituent modification." Dalton Transactions 47, no. 17 (2018): 6166–76. http://dx.doi.org/10.1039/c8dt00703a.

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New tris(phosphinomethyl)phenylborate ligands were synthesized to examine tuning of PhBP^Ph₃ donation via inductive modulation of the borate charge. Cyclic voltammetry suggests that rational tuning of this type occurs in complexes of zerovalent metals.

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24

Frogley, Benjamin J., Anthony F. Hill, Manab Sharma, Arup Sinha, and Jas S. Ward. "Semi-bridging σ-silyls as Z-type ligands." Chemical Communications 56, no. 24 (2020): 3532–35. http://dx.doi.org/10.1039/c9cc07763d.

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The reactions of SiHPh(NCH₂PPh₂)₂C₆H₄-1,2 with zerovalent group 10 reagents afford the homoleptic bimetallic complexes [M₂{μ-κ³-Si,P,P′-SiPh(CH₂PPh₂)₂C₆H₄}₂] (M = Ni, Pd, Pt) in which the M–M bond is unsymmetrically bridged by two σ-silyl groups.

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25

Jilek, Robert E., Giovanna Tripepi, Eugenijus Urnezius, William W. Brennessel, Victor G. Young, Jr., and John E. Ellis. "Zerovalent titanium–sulfur complexes. Novel dithiocarbamato derivatives of Ti(CO)6: [Ti(CO)4(S2CNR2)]−." Chem. Commun., no. 25 (2007): 2639–41. http://dx.doi.org/10.1039/b700808b.

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26

Malla, P. B., and S. Komarneni. "Oxide and Metal Intercalated Clay Nanocomposites." MRS Proceedings 286 (1992). http://dx.doi.org/10.1557/proc-286-323.

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ABSTRACTTruly nanocomposite materials that are stable to about 400 to 700°C can be prepared by intercalating oxides or metal clusters of about 0.4 to 2.0 nm in between ∼1.0 nm layers of smectite clays. Both the chemistry and size of intercalates (pillars) can be varied to introduce unique catalytic, molecular sieving, dehumidifying and adsorption properties in these materials. The intercalated clays also provide opportunities to prepare compositionally and stoichiometrically diverse nanocomposite precursors to high temperature structural and electronic ceramics. Although montmorillonite is the most widely used host, further designing in properties can be achieved by using other members of smectite family having subtle crystal chemical and compositional variations, such as beidellite, nontronite, saponite or hectorite. The sol-gel chemistry involving the preparation of positively charged mono- or multiphasic solution-sol or colloidal-sol particles is a viable approach to introduce chemically diverse oxide particles in the interlayers of smectite. Reduction of transition metal ions or complexes in the interlayers of smectite to zerovalent metal clusters/particles using polar liquids is another novel approach to develop catalytically active, high surface area materials.

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27

MANUTA, D. M., and A. J. LEES. "ChemInform Abstract: Solvatochromism of the Metal to Ligand Charge-Transfer Transitions of Zerovalent Tungsten Carbonyl Complexes." ChemInform 18, no. 2 (January 13, 1987). http://dx.doi.org/10.1002/chin.198702043.

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28

DARENSBOURG, D. J., K. M. SANCHEZ, J. H. REIBENSPIES, and A. L. RHEINGOLD. "ChemInform Abstract: Synthesis, Structure, and Reactivity of Zerovalent Group 6 Metal Pentacarbonyl Aryl Oxide Complexes. Reactions with Carbon Dioxide." ChemInform 20, no. 51 (December 19, 1989). http://dx.doi.org/10.1002/chin.198951228.

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29

Ha, Nguyen Van, Doan Thanh Dat, and Trieu Thi Nguyet. "Stereoelectronic Properties of 1,2,4-Triazole-Derived N-heterocyclic Carbenes - A Theoretical Study." VNU Journal of Science: Natural Sciences and Technology 35, no. 4 (December 23, 2019). http://dx.doi.org/10.25073/2588-1140/vnunst.4935.

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A theoretical study on stereo and electronic properties of a series of six 1,2,4-triazole-derived carbenes bearing different N4-substituents, namely isopropyl (1), benzyl (2), phenyl (3), mesityl (4), 2,6-diisopropylphenyl (5) and 1-naphthyl (6), has been carried out. Structures of the six carbenes were first optimized using Gaussian® 16 at B3LYP level. Their molecular geometries and electronic structures of the frontier orbitals were examined. The results suggest the similarity in nature of their HOMOs, which all posses s symmetry with respect to the heterocycle and essentially be the lone electron pair on the Ccarbene. Steric properties of the NHCs was also quantified using percent volume burried (%Vbur) approach. The NHC 1 with isopropyl N4-substituent was the least bulky one with %Vbur of 27.7 and the most sterically demanding carbene is 6, which has large 2,6-diisopropylphenyl substituent (%Vbur = 38.4). Interestingly, the NHCs with phenyl and 1-naphthyl N4-substituents display flexible steric hindrance due to possible rotation of the phenyl or 1-naphthyl around the N-C single bond. Beside stereoelectronic properties of the NHC, topographic steric map of their complexes with metal were also investigated. Keywords: N-heterocyclic carbene, triazolin-5-ylidene, stereoelectronic properties, percent volume burried. References [1] D. Bourissou, O. Guerret, F.P. Gabbaï, G. Bertrand, Stable Carbene, Chem. Rev. 100 (2000) 39−92. https://doi.org/10.1021/cr940472u.[2] N. Marion, S.P. Nolan, Well-Defined N-Heterocyclic Carbenes-Palladium(II) Precatalysts for Cross-Coupling Reactions, Acc. Chem. Res. 41 (2008) 1440−1449. https://doi.org/10.1021/ar800020y. [3] F.E. Hahn, M.C. Jahnke, Heterocyclic carbenes: synthesis and coordination chemistry, Angew. Chem., Int. Ed. 47 (2008) 3122−3172. http://doi. org/10.1002/anie.200703883. [4] M.N. Hopkinson, C. Richter, M. Schedler, F. Glorius, An overview of N-heterocyclic carbenes, Nature 510 (2014) 485−496. https://doi.org/nature13384.[5] W.A. Herrmann, N‐Heterocyclic Carbenes: A New Concept in Organometallic Catalysis, Angew. Chem., Int. Ed. 41 (2002) 1290−1309, https://doi.org/10.1002/1521-3773%2820020415%2941%3A8%3C1290%3A%3AAID-ANIE12 90%3E3.0.CO%3B2-Y.[6] S. Díez-Gonzalez, N. Marion, S.P. Nolan, N-Heterocyclic Carbenes in Late Transition Metal Catalysis, Chem. Rev. 109 (2009) 3612−3676. https://doi.org/10.1021/cr900074m.[7] L. Cavallo, A. Correa, C. Costabile, H.J. Jacobsen, Steric and electronic effects in the bonding of N-heterocyclic ligands to transition metals, Organomet. Chem. 690 (2005) 5407 -5413. https://doi.org/10.1016/j.jorganchem.2005. 07.012. [8] H. Clavier, S.P. Nolan, Percent buried volume for phosphine and N-heterocyclic carbeneligands: steric properties in organometallic chemistry, Chem. Commun. 46 (2010) 841−861. https://doi. org/10.1039/B922984A.[9] C. Buron, L. Stelzig, O. Guerret, H. 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