2009
DOI: 10.1021/om900841b
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Abstract: Novel gold(III) pyridinyl-oxazoline cationic complexes [Au(pyoxR)Cl2][X] [pyoxR = (S)-4-R-2-(pyridin-2-yl)-4,5-dihydrooxazole, with R = iPr, Bn, and (R)-4-phenyl-2-(pyridin-2-yl)-4,5-dihydrooxazole; X = PF6, AuCl4, or mixtures of the two anions] were synthesized and structurally characterized. Reaction of the adducts with NaOAc in aqueous solution afforded the neutral complexes [Au(N,N′,O)Cl] of the deprotonated ligands N-(1-hydroxy-3-R-2-yl)pyridine-2-carboxamide (R = iPr, Ph), N,N′H,OH, resulting from ring-o… Show more

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Cited by 27 publications
(29 citation statements)
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“…In fact, initial treatment of the pyridine‐oxazoline ligand 2 (Scheme b) with gold(III) (1 equiv. AuCl 3 ) gave 50 % conversion of the ligand into a new product, which was initially believed to be a Au(III) complex with AuCl 4 – as counterion, as reported for similar ligands . However, a new minor product was also selectively formed by reflux of ligand 2 and AuCl 3 in acetonitrile and was identified (XRD, Figure d) as the ammonium‐picolinate Au(I)Cl 2 complex, which is the similar ring opened product as described above (Figure c).…”
Section: Resultssupporting
confidence: 67%
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“…In fact, initial treatment of the pyridine‐oxazoline ligand 2 (Scheme b) with gold(III) (1 equiv. AuCl 3 ) gave 50 % conversion of the ligand into a new product, which was initially believed to be a Au(III) complex with AuCl 4 – as counterion, as reported for similar ligands . However, a new minor product was also selectively formed by reflux of ligand 2 and AuCl 3 in acetonitrile and was identified (XRD, Figure d) as the ammonium‐picolinate Au(I)Cl 2 complex, which is the similar ring opened product as described above (Figure c).…”
Section: Resultssupporting
confidence: 67%
“…The ring opening reaction was also observed by storage of the coordination solution of AuCl 3 and the 1b ligand in dichloromethane for 2–3 days. Corresponding ring opening of the oxazoline ring in the presence of water under weak basic conditions or during gold(III) coordination in aqueous media has been reported. In contrast to the presently observed aminocarboxylate complex formed by cleavage of C=N bond by water, we recently observed that oxazole ring opening by nucleophilic attack of strongly coordinating anions on 2 ‐Au(III) complexes gave a different outcome, as the nucleophilic CF 3 CO 2 – or NO 3 – anions attack the oxazoline‐CH 2 , to give cleavage of the oxazoline CH 2 ‐O bond …”
Section: Resultsmentioning
confidence: 81%
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“…p-Rich and p-deficient aromatics,w here starting materialsa nd productsa re both potentially viablel igands to transition metals, [54,55,56] react smoothly affording 9h-j despite the presence of Lewis basic atoms ( Table 2, entries 10-12).…”
Section: Resultsmentioning
confidence: 99%