Facile C–S, S–H, and S–S bond cleavage using a nickel(0) NHC complex

Citations Over TimeTop 10% of 2009 papers

Abstract

[Ni2(iPr2Im)4(COD)] 1 (iPr2Im = 1,3-di(isopropyl)-imidazol-2-ylidene) reacts at room temperature with the thioethers methyl para-tolyl sulfide, ethyl phenyl sulfide, benzothiophene and dibenzothiophene to afford the C-S bond cleavage products [Ni(iPr2Im)2(4-CH3-C6H4)(SMe)] 2, [Ni(iPr2Im)2(C6H5)(SEt)] 3, [Ni(iPr2Im)2(1,8-benzothiophenylato)] 4 and [Ni(iPr2Im)2(C,S-dibenzothiophenylato)] 5. In contrast to the reaction of thioethers or sulfoxides (reported earlier), no C-S bond cleavage was observed for the reaction of 1 with the sulfones bezothiophene-1,1-dioxide and methyl phenyl sulfone. In those cases the stable compounds [Ni(iPr2Im)2(eta2-2,3-benzothiophene-1,1-dioxide)] 6 and [Ni(iPr2Im)2(eta2-MeSO2C6H5)] 7 with a eta2-coordinated sulfone ligand have been isolated. Compound 6 has been structurally characterized. S-H bond cleavage was observed using 2-methyl-2-propanthiol to afford [Ni(iPr2Im)2(H)(StBu)] 8. The reaction of 1 with disulfides led to the dithiolato complexes [Ni(iPr2Im)2(SR)2] (R = tBu 9, Me 10, Ph 11) by S-S bond scission.

Related Papers

• → Demonstration of the carbon-sulfur bond targeted desulfurization of benzothiophene by thermophilicPaenibacillussp. strain A11-2 capable of desulfurizing dibenzothiophene(2000)88 cited
• → Catalytic Oxidation of Benzothiophene and Dibenzothiophene in Model Light Oil Ti-MWW(2006)47 cited
• → Effects of Solvents on Deep Hydrodesulfurization of Benzothiophene and Dibenzothiophene(1993)52 cited
• → Demonstration of the carbon-sulfur bond targeted desulfurization of benzothiophene by thermophilic Paenibacillus sp. strain A11-2 capable of desulfurizing dibenzothiophene(2000)8 cited
• → 97/04610 Partial oxidation of hydrocarbons over ceramic membrane reactor(1997)