Nickel-induced conversion of carbon-sulphur into carbon-carbon bonds. One-step transformations of enol sulphides into olefins and benzenethiol derivatives into alkylarenes and biaryls

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 14, 1979, Pages 637-638

  Wenkert, Ernest ^a   Ferreira, Tamis W ^a   Michelotti, Enrique L ^a  

^a RICE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049101088     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39790000637     Document Type: Article

References (5)

1. E. Wenkert, E. L. Michelotti, and C. S. Swindell; J. Amer. Chem. Soc., 1979, 101, 2246.
2. All reactions yield biphenyl as a minor by-product. In the reactions involving phenylmagnesium bromide it originates in the preparation of the Grignard reagent, whereas in the reactions with methylmagnesium and ρ-tolylmagnesium bromides it arises from the interaction of the Grignard reagent with the triphenylphosphine ligand of the catalyst M. L. H. Green, M. J. Smith, H. Felkin, and G. Swierczewski; Chem. Comm., 1971, 158.
3. Grignard reagents leave sulphides unaffected, act as bases towards thiols, alkyl sulphoxides, and alkyl sulphones, and behave as nucleophiles toward sulphoxides (M. S. Kharasch and O. Reinmuth; ‘Grignard Reactions of Nonmetallic Substances,’ Prentice-Hall, New York, 1954, p. 1296). None of these activities interfere with the nickel-induced reaction.
4. K. Tamao, K. Sumitani, Y. Kato, M. Zembayashi, A. Fujioka, S. Kodama, I. Nakajima, A. Minato, and M. Kumada; Bull. Chem. Soc. Japan, 1976, 49, 1958, and references therein.
5. Towards the end of this investigation there appeared a study of the nickel-catalysed reactions of alkenyl phenyl (or alkyl) sulphides in ether solvents (H. Okamura, M. Miura, and H. Takei; Tetrahedron Letters, 1979, 43) and we became aware of a report on nickel- catalysed reactions of alkenyl t-butyl sulphones with methylmagnesium halides in ether solvents (M. Julia, ‘Organic Synthesis with Sulphones,’ Plenary Lectures of the 8th International Symposium on Organic Sulphur Chemistry, Portoroz, Yugoslavia, June 1978, pp. 121-146). We thank Professor Julia for drawing our attention to the latter work.