Aluminum chloride-iron promoted coupling of sulfonyl chlorides with alkyl halides in aqueous media

Chemistry Letters

Volumn , Issue 6, 2001, Pages 512-513

  Saikia, Promod ^a   Laskar, Dhrubojyoti D ^a   Prajapati, Dipak ^a   Sandhu, Jagir S ^a  

^a REGIONAL RESEARCH LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035533929     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2001.512     Document Type: Article

References (22)

1. B. M. Trost, Bull. Chem. Soc., Jpn., 61, 107 (1988).
2. For a review of sulfone chemistry see: B. M. Trost, "Comprehensive Organic Synthesis," Pergamon Press, Oxford, (1991), Vol. 6, p. 157; P. D. Magnus, Tetrahedron, 33, 2019 (1977).
3. For a review of sulfone chemistry see: B. M. Trost, "Comprehensive Organic Synthesis," Pergamon Press, Oxford, (1991), Vol. 6, p. 157; P. D. Magnus, Tetrahedron, 33, 2019 (1977).
4. For reports on Pd- and Te-catalyzed coupling reaction of sulfonyl chlorides see: S. S. Labadie, J. Org. Chem., 54, 2496 (1989); using tetra-n-butylammonium oxone see: B. M. Trost, and R. Braslace, J. Org. Chem., 53, 532 (1988); H. Suzuki, Y. S. I. Nishioka, S. I. Padmanabhan, and T. Ogawa, Chem. Lett., 1988, 727; using fluorides catalyst see: A. A. Kolomeitsev, V. N. Movchun, N. V. Kondratenko, and Y. L. Yagupolski, Synthesis, 1990, 1151; using Aliquat 336 see: G. Bram, A. Loupy, M. C. Roux-Schmitt, J. Sansoulet, T. Strzalko, and J. Seyden-Penne, Synthesis, 1987, 56; using sodium formaldehyde sulfoxylate see: A. R. Harris, Synth. Commun., 18, 659 (1988); for a more recent multistep report using (phenylsulfonyl)-1,2-propadiene see: A. Padwa and P. E. Yeske, J. Org. Chem., 56, 6386 (1991).
5. For reports on Pd- and Te-catalyzed coupling reaction of sulfonyl chlorides see: S. S. Labadie, J. Org. Chem., 54, 2496 (1989); using tetra-n-butylammonium oxone see: B. M. Trost, and R. Braslace, J. Org. Chem., 53, 532 (1988); H. Suzuki, Y. S. I. Nishioka, S. I. Padmanabhan, and T. Ogawa, Chem. Lett., 1988, 727; using fluorides catalyst see: A. A. Kolomeitsev, V. N. Movchun, N. V. Kondratenko, and Y. L. Yagupolski, Synthesis, 1990, 1151; using Aliquat 336 see: G. Bram, A. Loupy, M. C. Roux-Schmitt, J. Sansoulet, T. Strzalko, and J. Seyden-Penne, Synthesis, 1987, 56; using sodium formaldehyde sulfoxylate see: A. R. Harris, Synth. Commun., 18, 659 (1988); for a more recent multistep report using (phenylsulfonyl)-1,2-propadiene see: A. Padwa and P. E. Yeske, J. Org. Chem., 56, 6386 (1991).
6. For reports on Pd- and Te-catalyzed coupling reaction of sulfonyl chlorides see: S. S. Labadie, J. Org. Chem., 54, 2496 (1989); using tetra-n-butylammonium oxone see: B. M. Trost, and R. Braslace, J. Org. Chem., 53, 532 (1988); H. Suzuki, Y. S. I. Nishioka, S. I. Padmanabhan, and T. Ogawa, Chem. Lett., 1988, 727; using fluorides catalyst see: A. A. Kolomeitsev, V. N. Movchun, N. V. Kondratenko, and Y. L. Yagupolski, Synthesis, 1990, 1151; using Aliquat 336 see: G. Bram, A. Loupy, M. C. Roux-Schmitt, J. Sansoulet, T. Strzalko, and J. Seyden-Penne, Synthesis, 1987, 56; using sodium formaldehyde sulfoxylate see: A. R. Harris, Synth. Commun., 18, 659 (1988); for a more recent multistep report using (phenylsulfonyl)-1,2-propadiene see: A. Padwa and P. E. Yeske, J. Org. Chem., 56, 6386 (1991).
7. For reports on Pd- and Te-catalyzed coupling reaction of sulfonyl chlorides see: S. S. Labadie, J. Org. Chem., 54, 2496 (1989); using tetra-n-butylammonium oxone see: B. M. Trost, and R. Braslace, J. Org. Chem., 53, 532 (1988); H. Suzuki, Y. S. I. Nishioka, S. I. Padmanabhan, and T. Ogawa, Chem. Lett., 1988, 727; using fluorides catalyst see: A. A. Kolomeitsev, V. N. Movchun, N. V. Kondratenko, and Y. L. Yagupolski, Synthesis, 1990, 1151; using Aliquat 336 see: G. Bram, A. Loupy, M. C. Roux-Schmitt, J. Sansoulet, T. Strzalko, and J. Seyden-Penne, Synthesis, 1987, 56; using sodium formaldehyde sulfoxylate see: A. R. Harris, Synth. Commun., 18, 659 (1988); for a more recent multistep report using (phenylsulfonyl)-1,2-propadiene see: A. Padwa and P. E. Yeske, J. Org. Chem., 56, 6386 (1991).
8. For reports on Pd- and Te-catalyzed coupling reaction of sulfonyl chlorides see: S. S. Labadie, J. Org. Chem., 54, 2496 (1989); using tetra-n-butylammonium oxone see: B. M. Trost, and R. Braslace, J. Org. Chem., 53, 532 (1988); H. Suzuki, Y. S. I. Nishioka, S. I. Padmanabhan, and T. Ogawa, Chem. Lett., 1988, 727; using fluorides catalyst see: A. A. Kolomeitsev, V. N. Movchun, N. V. Kondratenko, and Y. L. Yagupolski, Synthesis, 1990, 1151; using Aliquat 336 see: G. Bram, A. Loupy, M. C. Roux-Schmitt, J. Sansoulet, T. Strzalko, and J. Seyden-Penne, Synthesis, 1987, 56; using sodium formaldehyde sulfoxylate see: A. R. Harris, Synth. Commun., 18, 659 (1988); for a more recent multistep report using (phenylsulfonyl)-1,2-propadiene see: A. Padwa and P. E. Yeske, J. Org. Chem., 56, 6386 (1991).
9. For reports on Pd- and Te-catalyzed coupling reaction of sulfonyl chlorides see: S. S. Labadie, J. Org. Chem., 54, 2496 (1989); using tetra-n-butylammonium oxone see: B. M. Trost, and R. Braslace, J. Org. Chem., 53, 532 (1988); H. Suzuki, Y. S. I. Nishioka, S. I. Padmanabhan, and T. Ogawa, Chem. Lett., 1988, 727; using fluorides catalyst see: A. A. Kolomeitsev, V. N. Movchun, N. V. Kondratenko, and Y. L. Yagupolski, Synthesis, 1990, 1151; using Aliquat 336 see: G. Bram, A. Loupy, M. C. Roux-Schmitt, J. Sansoulet, T. Strzalko, and J. Seyden-Penne, Synthesis, 1987, 56; using sodium formaldehyde sulfoxylate see: A. R. Harris, Synth. Commun., 18, 659 (1988); for a more recent multistep report using (phenylsulfonyl)-1,2-propadiene see: A. Padwa and P. E. Yeske, J. Org. Chem., 56, 6386 (1991).
10. For reports on Pd- and Te-catalyzed coupling reaction of sulfonyl chlorides see: S. S. Labadie, J. Org. Chem., 54, 2496 (1989); using tetra-n-butylammonium oxone see: B. M. Trost, and R. Braslace, J. Org. Chem., 53, 532 (1988); H. Suzuki, Y. S. I. Nishioka, S. I. Padmanabhan, and T. Ogawa, Chem. Lett., 1988, 727; using fluorides catalyst see: A. A. Kolomeitsev, V. N. Movchun, N. V. Kondratenko, and Y. L. Yagupolski, Synthesis, 1990, 1151; using Aliquat 336 see: G. Bram, A. Loupy, M. C. Roux-Schmitt, J. Sansoulet, T. Strzalko, and J. Seyden-Penne, Synthesis, 1987, 56; using sodium formaldehyde sulfoxylate see: A. R. Harris, Synth. Commun., 18, 659 (1988); for a more recent multistep report using (phenylsulfonyl)-1,2-propadiene see: A. Padwa and P. E. Yeske, J. Org. Chem., 56, 6386 (1991).
11. E. Block, in "The Chemistry of Functional Groups," E. Supplement, Part 1, ed. by S. Patai, Wiley, New York (1980), chap. 13; J. Smeek and J. S. Fowler, J. Org. Chem., 33, 3422 (1968).
12. E. Block, in "The Chemistry of Functional Groups," E. Supplement, Part 1, ed. by S. Patai, Wiley, New York (1980), chap. 13; J. Smeek and J. S. Fowler, J. Org. Chem., 33, 3422 (1968).
13. Y. Yamamoto and N. Asao, Chem. Rev., 93, 2307 (1993); C. J. Li, Chem. Rev., 93, 2023 (1993); A. Lubineau, J. Auge, and Y. Queneau, Synthesis, 1994, 741; C. J. Li, Tetrahedron, 52, 5643 (1996).
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15. Y. Yamamoto and N. Asao, Chem. Rev., 93, 2307 (1993); C. J. Li, Chem. Rev., 93, 2023 (1993); A. Lubineau, J. Auge, and Y. Queneau, Synthesis, 1994, 741; C. J. Li, Tetrahedron, 52, 5643 (1996).
16. Y. Yamamoto and N. Asao, Chem. Rev., 93, 2307 (1993); C. J. Li, Chem. Rev., 93, 2023 (1993); A. Lubineau, J. Auge, and Y. Queneau, Synthesis, 1994, 741; C. J. Li, Tetrahedron, 52, 5643 (1996).
17. L. A. Paquette and T. M. Mitzel, J. Am. Chem. Soc., 118, 1931 (1996); L. A. Paquette and P. C. Lobben, J. Am. Chem. Soc., 118, 1917 (1996); C. J. Li, D. L. Chen, Y. Q. Lu, J. X. Haberman, and J. T. Mague, J. Am. Chem. Soc., 118, 4216 (1996).
18. L. A. Paquette and T. M. Mitzel, J. Am. Chem. Soc., 118, 1931 (1996); L. A. Paquette and P. C. Lobben, J. Am. Chem. Soc., 118, 1917 (1996); C. J. Li, D. L. Chen, Y. Q. Lu, J. X. Haberman, and J. T. Mague, J. Am. Chem. Soc., 118, 4216 (1996).
19. L. A. Paquette and T. M. Mitzel, J. Am. Chem. Soc., 118, 1931 (1996); L. A. Paquette and P. C. Lobben, J. Am. Chem. Soc., 118, 1917 (1996); C. J. Li, D. L. Chen, Y. Q. Lu, J. X. Haberman, and J. T. Mague, J. Am. Chem. Soc., 118, 4216 (1996).
20. L. L. Frye, E. L. Sullivan, K. P. Cusack and J. M. Funaro, J. Org. Chem., 57, 697 (1992); S. S. Labadie, J. Org. Chem., 54, 2496 (1989).
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22. Aluminum chloride and iron powder used were of commercial grade and procured from Central Drug House (Pvi) Ltd., New Delhi-110 002; sulfonyl chlorides used were obtained commercially and distilled before use.