Cyclometalated gold(III) iminophosphoranes which incorporate carbohydrate groups

Jarman, Bevan P.; Nicholson, Brian K.

doi:10.1016/j.jorganchem.2011.11.009

Cited by 4 publications

(1 citation statement)

References 43 publications

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“…Examples of Au(III) complexes with carbohydrate ligands are more rare [13] . For instance, the groups of Nicholson and de Almeida reported the synthesis of some Au(III) complexes containing, respectively, glycosyl iminophosphoranes [13a] and derivatives of d ‐galactose, d ‐ribose and d ‐glucono‐1,5‐lactone [13b]…”

Section: Introductionmentioning

confidence: 99%

New Water‐Soluble Au(III) Complexes with Xyloside‐Based Ligands: Synthesis, Structural Characterization, Solution Studies and Catalytic Evaluation

et al. 2023

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A short and convenient approach to the original xyloside-based ligands, has been achieved, using d-xylose as a starting material. The complexation properties of these ligands towards Au(III) cations were studied by different methods, such as multinuclear NMR, mass spectrometry, elemental analysis. A preliminary study using protometric titrations has been carried out in aqueous solution under various pH conditions, thus in order to investigate the binding of Au(III) cations to these ligands. Furthermore, molecular calculations were performed to obtain additional structural information. The catalytic activity of the most stable Au(III) complexes was evaluated for the homogeneous reduction of 4-nitrophenol (4-NP) to 4-aminophenol (4-AP) in the presence of NaBH 4 .

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Section: Introductionmentioning

confidence: 99%

New Water‐Soluble Au(III) Complexes with Xyloside‐Based Ligands: Synthesis, Structural Characterization, Solution Studies and Catalytic Evaluation

et al. 2023

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Direct Use of Benzylic Alcohols for Gold(III)‐Catalyzed S‐Benzylation of Mercaptobenzoic Acids in Water

et al. 2016

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We demonstrate the gold(III)-catalyzed direct substitution of benzylic alcohols in water. These atom economic and environmentally benign protocols afford S-benzylated productsi nm oderate to excellent yields.I nc ontrast, common Lewis or Brønsted acids as catalyst, ando rganic solventss uch as dichloromethane or toluene were ineffectivef or the S-benzylation of mercaptobenzoic acids.W ater can be an attractive toolf or newt ransitionm etalcatalyzed reactions.AHammetts tudy for the rate constants with various substituted alcohols shows ag ood correlation (R 2 = 0.97) between the log(k X / k H )a nd the s + + value of the respective substituents. From the slope negative 1 valueso f2 .35 are ob-tained,s uggesting that there is ab uild-up of positive charge in the transitions tate.O ur catalytic system can be performed with the use of only 2mol% of gold(III) catalyst without any other additives in water, and scaled up to 10 mmol scale (85% isolated yield). Notably,t he present method can accomplish the S-benzylation of unprotected mercaptobenzoic acids,w hich is chemoselective andl eaves the carboxyl group intact. Furthermore,t he direct substitution of allylica nd propargylic alcohols also proceeded smoothlyi ngoody ields.

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Coordination chemistry of the thiosalicylate ligand

Wehr-Candler

Henderson

2016

Coordination Chemistry Reviews

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Cyclometalated gold(III) iminophosphoranes which incorporate carbohydrate groups

Cited by 4 publications

References 43 publications

New Water‐Soluble Au(III) Complexes with Xyloside‐Based Ligands: Synthesis, Structural Characterization, Solution Studies and Catalytic Evaluation

New Water‐Soluble Au(III) Complexes with Xyloside‐Based Ligands: Synthesis, Structural Characterization, Solution Studies and Catalytic Evaluation

Direct Use of Benzylic Alcohols for Gold(III)‐Catalyzed S‐Benzylation of Mercaptobenzoic Acids in Water

Coordination chemistry of the thiosalicylate ligand

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