Metal complexes of saccharin

Oxidative-addition of the N–H bond of saccharin (sacH) to a triosmium centre: Synthesis, structure and reactivity of Os3(CO)10(μ-H)(μ-sac)

“…The reactivity of this sac-bridged triosmium cluster towards various monodentate phosphines has also been investigated. 2) with saccharin: Oxidative-addition of N-H bond at triosmium centres 4 In early 1980s, Johnson and Lewis investigated the reactivity of Os3(CO)10(NCMe)2 towards acyclic amides, RCONH2 (R = H, Me, Et, Pr, Ph) [9], N-H oxidative-addition resulting in formation of Os3(CO)10(μ-H)(μ-HNCOR), which were characterized on the on the basis of spectroscopic data [9]. The cyclic amide saccharin (sacH) likewise reacts with Os3(CO)10(NCMe)2 under similar conditions.…”

“…The coordination chemistry of the sac has been extensively investigated revealing its versatile coordination properties as it possesses four donor atoms to bind with transition metal centres -one nitrogen and three oxygens (one carbonylic and two sulfonic) [2]. Although it can bind to transition metals in a number of different ways using these donor atoms, the simple Nbound coordination (I in Chart 1) is by far the most commonly observed [2,3].…”

Unusual saccharin-N,O (carbonyl) coordination in mixed-ligand copper(II) complexes: Synthesis, X-ray crystallography and biological activity

“…Saccharin is also of interest to synthetic chemists because of its ability to act as a polyfunctional ligand [5]. The coordination chemistry of the saccharin anion is very interesting as its donor atoms can chelate to a metallic centre in different modes, via the imino-nitrogen, carbonyl-or sulfonyl-oxygen atoms and can generate either N-or O-or Smonodentate or (N,O)-bidentate chelating complexes [4].…”

“…Mixed-ligand complexes are formed when the metal ion binds to two different ligand moieties. However, there have also been published reports on the coordination of metal cations with the carbonyl-or sulfonyl-oxygen of saccharin [5]; although the latter is less basic and is rarely involved in bonding. A comparatively rare (N,O)-bidentate bridging coordination mode, that is reported for one of the complexes in this study, has been found in only three examples in the literature [7,8,9].…”

A green solventless protocol for Michael addition of phthalimide and saccharin to acrylic acid esters in the presence of zinc oxide as a heterogeneous and reusable catalyst

“…, Cu 2+ and etc. 6 Conjugate addition of phthalimide and saccharin to α,β-unsaturated esters also affords protected β-amino acids. This class of compounds are essential components in many bioactive compounds and drugs scaffolds, including β-peptides, 7 imeriamine (hypoglycemic and antiketogenic agent, Figure 1), 8 vitamin B 3 ( Figure 1), 9 cryptophycin (antitumor), 10 and TAN-1057 A (antibiotic).…”