Catalytic Action of Triarylstibanes: Oxidation of Benzoins into Benzyls Using Triarylstibanes Under an Aerobic Condition

Abstract

Benzoins are simply oxidized to benzils in excellent yields with a catalytic amount of triarylstibanes under an aerobic condition. This catalytic oxidation is heteroatom-specific in the antimony compound and no reaction take place with other group 15 reagents such as triphenylphosphane, -arsane and -bismuthane. The reaction should involve an oxidation-reduction cycle between stibane Sb(III) and stiborane Sb(V) under air.

Structural analysis of organometallic compounds with soft ionization mass spectrometry

“…The most important properties of these compounds become apparent, their participation in many stechiometric and catalytical reactions (e.g., cross-coupling reactions) are used to implement different chemical groups into the molecular structure. Mainly transitionmetal complexes, but also organometallics with bismuth, antimony, tin, and other metals, are used for this purpose (Rao et al, 2002;Hocek, 2003;Netherton & Fu, 2004;Yasuike et al, 2005). Organotin compounds are also used as stabilizers of rigid polyvinyl chloride against photochemical and thermal transformations (Kizlink, 1996).…”

“…Organotin compounds are also used as stabilizers of rigid polyvinyl chloride against photochemical and thermal transformations (Kizlink, 1996). It is also worth mentioning the applications in photocatalytical and asymmetrical reactions (Noyori, 2002;Yasuike et al, 2005).…”

Antimony/N‐Hydroxyphthalimide as a Catalyst System for Cross‐Dehydrogenative Coupling Reactions under Aerobic Conditions

“…However, in most cases, antimony served as an additive for other transition metal catalysts (V, Mo, Fe, etc.) and very high temperatures were required for these reactions 17. Although antimony is not strictly a non‐metal, we decided to investigate this catalyst further, since the catalytic use of antimony for the CDC reactions of tertiary amines has not been reported 18.…”

Synthesis, Structure and Applications of Hypervalent Organoantimony Compounds Having Intramolecular E→Sb (E = N, O, S) Coordinations

“…However, triethylantimony is spontaneously flammable in air, and it is not until 1882 that the development of organoantimony chemistry began when air-stable triphenylantimony was synthesized by Michaelis and Reese [2]. Since then, a large number of organoantimony compounds of trivalent and pentavalent states were synthesized, and used in areas such as medicine [3], catalysis [4][5][6], organic synthesis [7][8][9][10] and ligand chemistry [11][12][13]. However, wide application is restricted due to the unstable nature of the compounds, a result of being air-sensitive and/or ligand scrambling.…”