Synthesis 1990; 1990(2): 89-103
DOI: 10.1055/s-1990-26798
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Transition-Metal-Mediated C-S Bond Cleavage Reactions

Tien-Yau Luh* , Zhi-Jie Ni
  • *Department of Chemistry, National Taiwan University, Taipei, Taiwan, 10764 Republic of China
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Publication History

Publication Date:
17 September 2002 (online)

The transformations of carbon-sulfur bonds into carbon-hydrogen and carbon-carbon bonds under homogeneous conditions are discussed. The reduction methods using metal carbonyls, low-valent transition metal complexes, metal hydrides, Grignard reagents and transition metal compounds as reducing agents are presented. The reactions leading to the carbon-carbon bond formation by coupling with main group orgnometallic nucleophiles, desulfurdimerization, carbonylation and related methods are reviewed. Some other synthetically useful reactions involving the cleavage of carbon-sulfur bonds are also briefly discussed. 1. Introduction 2. Reduction of C-S Bonds with Metal Carbonyls 2.1 Desulfurization of Thiols 2.2 Desulfurization of Sulfides 3. Reduction of C-S Bonds with Complex Hydrides in the Presence of Transition Metal Compounds 4. Miscellaneous Reduction Methods 5. Coupling Reactions with Organometallic Nucleophiles 5.1 Sulfides 5.2 Dithioacetals 5.3 Thiols 5.4 Sulfoxides, Sulfones and Related Reactions 6. Desulfurdimerization Reactions 7. Carbonylation Reactions 8. Miscellaneous Reactions