By Remi Chauvin, Yves Canac
Contents: Yves Canac and Remi Chauvin: impartial eta1-carbon ligands: past carbon monoxide; Esteban P. Urriolabeitia: Ylide Ligands; Wolfgang Petz and Gernot Frenking: Carbodiphosphoranes and similar ligands; Mareike C. Jahnke and F. Ekkehardt Hahn: Chemistry of N-Heterocyclic Carbene Ligands; Tsuyoshi Kato, Eddy Maerten, Antoine Baceiredo: Non-NHCs reliable singlet carbene ligands; Victorio Cadierno, Sergio E. García-Garrido: All-Carbon-Substituted Allenylidene and comparable Cumulenylidene Ligands; Victorio Cadierno, Sergio E. García-Garrido: Heteroatom-Conjugated Allenylidene and similar Cumulenylidene Ligands.
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Extra resources for Transition Metal Complexes of Neutral eta1-Carbon Ligands (Topics in Organometallic Chemistry)
The “in situ” generated ylide binds to the metal center replacing the acac ligand, which is liberated under its protonated form. Examples are shown in Scheme 7. In some cases, even the methyl group can be sequentially deprotonated. Treatment of the sulfoxonium salt [Me3SO]ClO4 with [acacAuPPh3] gives a simple substitution product (17). Further reaction of (17) with [acacAuPPh3] allows the complete deprotonation of the methyl group and the synthesis of trinuclear (18), which can incorporate an additional [AuPPh3]+ cationic fragment and give an hypercoordinate ylidic Ca atom in (19) [73, 74].
Gandelman M, Rybtchinski B, Ashkenazi N, Gauvin RM, Mistein D (2001) J Am Chem Soc 123:5372 97. Gandelman M, Naing KM, Rybtchinski B, Poverenov E, Ben David Y, Ashkenazi N, Gauvin RM, Milstein D (2005) J Am Chem Soc 127:15265 98. Falvello LR, Llusar R, Margalejo ME, Navarro R, Urriolabeitia EP (2003) Organometallics 22:1132 99. Vicente J, Chicote MT, MacBeath C, Ferna´ndez Baeza J, Bautista D (1999) Organometallics 18:2677 100. Vicente J, Chicote MT, MacBeath C, Jones PG (2003) Organometallics 22:1843 101.
Urriolabeitia Me5 Me5 PPh3 Ru PPh3 C PPh3 Ru Me Os Ph3P N P Ph2 phosphine + vinylidene PPh3 Os PPh3 H SiMe3 Me3Si P Ph2 (75) Me3Si (74) Scheme 21 Orthometallation of ylides; ruthenium and osmium examples H Cl NCMe, Δ Pd Ph2P 2+ Ph3P 2+ O L Cl 2L Pd 2 PPh3 (77) Cl O H O Pd 2 Ph2P CH2Cl2, rt Ph3P PPh3 (78) 2 (76) Scheme 22 Different ways to promote orthometallation on Pd(bis ylide) complexes 2+ O PPh3 Ph3P 2+ Ph3P PtCl2 PPh3 Ph3P PtCl2 PtCl2 2+ Cl Ph2P Cl Pt Ph2P Cl Ph Pt Cl Pt Ph2P PPh2 O PPh3 (79) 2 (80) (81) Scheme 23 Different orthoplatination reactions from ylide and phosphonium salts of PtCl2 with Ph3P=CHC(O)Me was expected to give the coordination product (1) , but the actual reaction product is the orthoplatinated (73) .
Transition Metal Complexes of Neutral eta1-Carbon Ligands (Topics in Organometallic Chemistry) by Remi Chauvin, Yves Canac