Anchoring rhodium(I) on benzoylthiourea-functionalized silica xerogels. Production of recyclable hydroformylation catalysts and the crystal structure of the model compound [Rh(cod)(Hbztu)Cl]

Cauzzi, Daniele; Lanfranchi, Maurizio; Marzolini, Giovanna; Predieri, Giovanni; Tiripicchio, António; Costa, Mirco; Zanoni, R.

doi:10.1016/0022-328x(94)00009-2

Cited by 36 publications

(37 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This lengthening of the S-C bond is consistent with the decreasing double bond character due to the coordination at the metal center. (Cauzzi et al, 1995(Cauzzi et al, , 1997. The syn conformation of the substituent on the sulfur with respect to the chlorine atom is stabilized by the intramolecular N(1)-H(1)···Cl(1) hydrogen bonding interaction.…”

Section: Commentmentioning

confidence: 97%

See 1 more Smart Citation

Chlorido(η⁴-cycloocta-1,5-diene)(N,N′-diethylthiourea-κS)rhodium(I)

et al. 2010

View full text Add to dashboard Cite

In the title rhodium(I) complex, [RhCl(C8H12)(C5H12N2S)], N,N′-diethylthiourea acts as a monodenate S-donor ligand. The rhodium(I) coordination sphere is completed by the Cl atom and the COD [= 1,5-cyclooctadiene] ligand interacting through the π-electrons of the double bonds. If the midpoints of these two bonds are taken into account, the Rh atom exhibits a distorted square-planar coordination. The syn conformation of the N,N′-diethylthiourea ligand with respect to the Cl atom is stabilized by an intramolecular N—H⋯Cl hydrogen bond. A weak intermolecular N—H⋯Cl interaction links molecules along the a axis.

show abstract

Section: Commentmentioning

confidence: 97%

“…For the application of thioureas as ligands for metal precursors in asymmetric catalysis, see: Breuzard et al (2000). For related Rh(I) complexes containing thiourea ligands, see: Cauzzi et al (1995Cauzzi et al ( , 1997. For structural data of the N,N 0 -diethylthiourea ligand, see: Ramnathan et al (1995).…”

Section: Related Literaturementioning

confidence: 99%

Chlorido(η⁴-cycloocta-1,5-diene)(N,N′-diethylthiourea-κS)rhodium(I)

et al. 2010

View full text Add to dashboard Cite

show abstract

“…For related Rh(I) complexes containing thiourea ligands, see: Cauzzi et al (1995); Kemp et al (1996Kemp et al ( , 1997; Roodt et al (1994). For related Rh(I) complexes containing other or similar -diketones and -bonding ligands, see: Bahl et al (2000); Brink et al (2007a,b); Leipoldt et al (1977Leipoldt et al ( , 1980; Roodt et al (2003); Steyl et al (2004).…”

Section: Related Literaturementioning

confidence: 99%

(N-Benzoyl-N′-phenylthiourea-κS)chlorido(η⁴-1,5-cyclooctadiene)rhodium(I)

et al. 2010

View full text Add to dashboard Cite

The title compound, [RhCl(C8H12)(C14H12N2OS)], is a rhodium(I) derivative with a functionalized thiourea ligand. Despite the presence of several heteroatoms, the thiourea ligand coordinates only in a monodentate fashion via the S atom. The geometry of the coordination sphere is approximately square planar about the RhI atom, with two bonds to the π-electrons of the 1,5-cyclooctadiene ligand, one bond to the Cl− ligand and one bond to the S atom of the thiourea ligand. The molecular structure is stabilized by intramolecular N—H⋯O and N—H⋯Cl hydrogen bonding. Intermolecular N—H⋯O hydrogen-bonding interactions lead to the formation of layers extending parallel to (011).

show abstract

“…However, the ligand‐accelerated Pd II ‐catalyzed bis(methoxycarbonylation) of olefins has relied principally on nitrogen‐ and phosphorus‐based auxiliaries,21−23 and no other types of ligands have been described in the literature. Recently, we have witnessed the increased application of thiourea derivatives as ligands and catalysts in organic synthesis;24−31 the palladium−thiourea catalyzed carbonylation of terminal alkynes and allylic alcohols by Chiusoli is particularly attractive 32,33. Our own experience in using [Pd(tu) 4 ]I 2 (tu = thiourea) as an effective catalyst in the palladium‐catalyzed carbonylative annulation illustrated that thiourea is stable under a variety of oxidative conditions, and that no palladium precipitation occurred 34,35.…”

Section: Introductionmentioning

confidence: 99%