A Direct Synthesis of 2-(Trimethylstannyl)pyrroles from Michael Acceptors and Stannylated Tosylmethyl Isocyanide

Journal of Organic Chemistry

Volumn 63, Issue 16, 1998, Pages 5332-5338

  Dijkstra, Harm P ^a   Ten Have, Ronald ^a   Van Leusen, Albert M ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000109604     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo972216y     Document Type: Article

References (33)

1. Chemistry of Sulfonylmethyl Isocyanides. 45. For part 44, see: ten Have, R.; van Leusen, A. M. Tetrahedron 1998, 54, 1913.
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3. (b) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652.
4. See refs 2b, 6, 7, and 8.
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6. Some references are as follows: (a) Possel, O.; van Leusen, A. M. Heterocycles 1977, 7, 77. (b) Moskal, J.; van Leusen, A. M. J. Org. Chem. 1986, 51, 4131. Magnus, P.; Gallagher, T.; Schultz, J.; Or, Y.-S.; Ananthanarayan, T. P. J. Am. Chem. Soc. 1987, 109, 2706. (d) van Leusen, D.; Flentge, E.; van Leusen, A. M. Tetrahedron 1991, 47, 4639. (e) van Leusen, D.; van Echten, E.; van Leusen, A. M. J. Org. Chem. 1992, 57, 2245. (f) Dell'Erba, C.; Giglio, A.; Mugnoli, A.; Novi, M.; Petrillo, G.; Stagnaro, P. Tetrahedron 1995, 51, 5181. (g) van Leusen, A. M.; van Leusen, D. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995; Vol. 7, p 4973. (h) van Leusen, A. M.; van Leusen, D. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995, Vol. 5, p 3650. ten Have, R.; Leusink, F. R.; van Leusen, A. M. Synthesis 1996, 871. For an exhaustive account, see: (J) van Leusen, D.; van Leusen, A. M. Org. React, in press.
7. Some references are as follows: (a) Possel, O.; van Leusen, A. M. Heterocycles 1977, 7, 77. (b) Moskal, J.; van Leusen, A. M. J. Org. Chem. 1986, 51, 4131. Magnus, P.; Gallagher, T.; Schultz, J.; Or, Y.-S.; Ananthanarayan, T. P. J. Am. Chem. Soc. 1987, 109, 2706. (d) van Leusen, D.; Flentge, E.; van Leusen, A. M. Tetrahedron 1991, 47, 4639. (e) van Leusen, D.; van Echten, E.; van Leusen, A. M. J. Org. Chem. 1992, 57, 2245. (f) Dell'Erba, C.; Giglio, A.; Mugnoli, A.; Novi, M.; Petrillo, G.; Stagnaro, P. Tetrahedron 1995, 51, 5181. (g) van Leusen, A. M.; van Leusen, D. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995; Vol. 7, p 4973. (h) van Leusen, A. M.; van Leusen, D. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995, Vol. 5, p 3650. ten Have, R.; Leusink, F. R.; van Leusen, A. M. Synthesis 1996, 871. For an exhaustive account, see: (J) van Leusen, D.; van Leusen, A. M. Org. React, in press.
8. Some references are as follows: (a) Possel, O.; van Leusen, A. M. Heterocycles 1977, 7, 77. (b) Moskal, J.; van Leusen, A. M. J. Org. Chem. 1986, 51, 4131. Magnus, P.; Gallagher, T.; Schultz, J.; Or, Y.-S.; Ananthanarayan, T. P. J. Am. Chem. Soc. 1987, 109, 2706. (d) van Leusen, D.; Flentge, E.; van Leusen, A. M. Tetrahedron 1991, 47, 4639. (e) van Leusen, D.; van Echten, E.; van Leusen, A. M. J. Org. Chem. 1992, 57, 2245. (f) Dell'Erba, C.; Giglio, A.; Mugnoli, A.; Novi, M.; Petrillo, G.; Stagnaro, P. Tetrahedron 1995, 51, 5181. (g) van Leusen, A. M.; van Leusen, D. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995; Vol. 7, p 4973. (h) van Leusen, A. M.; van Leusen, D. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995, Vol. 5, p 3650. ten Have, R.; Leusink, F. R.; van Leusen, A. M. Synthesis 1996, 871. For an exhaustive account, see: (J) van Leusen, D.; van Leusen, A. M. Org. React, in press.
9. Some references are as follows: (a) Possel, O.; van Leusen, A. M. Heterocycles 1977, 7, 77. (b) Moskal, J.; van Leusen, A. M. J. Org. Chem. 1986, 51, 4131. Magnus, P.; Gallagher, T.; Schultz, J.; Or, Y.-S.; Ananthanarayan, T. P. J. Am. Chem. Soc. 1987, 109, 2706. (d) van Leusen, D.; Flentge, E.; van Leusen, A. M. Tetrahedron 1991, 47, 4639. (e) van Leusen, D.; van Echten, E.; van Leusen, A. M. J. Org. Chem. 1992, 57, 2245. (f) Dell'Erba, C.; Giglio, A.; Mugnoli, A.; Novi, M.; Petrillo, G.; Stagnaro, P. Tetrahedron 1995, 51, 5181. (g) van Leusen, A. M.; van Leusen, D. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995; Vol. 7, p 4973. (h) van Leusen, A. M.; van Leusen, D. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995, Vol. 5, p 3650. ten Have, R.; Leusink, F. R.; van Leusen, A. M. Synthesis 1996, 871. For an exhaustive account, see: (J) van Leusen, D.; van Leusen, A. M. Org. React, in press.
10. Some references are as follows: (a) Possel, O.; van Leusen, A. M. Heterocycles 1977, 7, 77. (b) Moskal, J.; van Leusen, A. M. J. Org. Chem. 1986, 51, 4131. Magnus, P.; Gallagher, T.; Schultz, J.; Or, Y.-S.; Ananthanarayan, T. P. J. Am. Chem. Soc. 1987, 109, 2706. (d) van Leusen, D.; Flentge, E.; van Leusen, A. M. Tetrahedron 1991, 47, 4639. (e) van Leusen, D.; van Echten, E.; van Leusen, A. M. J. Org. Chem. 1992, 57, 2245. (f) Dell'Erba, C.; Giglio, A.; Mugnoli, A.; Novi, M.; Petrillo, G.; Stagnaro, P. Tetrahedron 1995, 51, 5181. (g) van Leusen, A. M.; van Leusen, D. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995; Vol. 7, p 4973. (h) van Leusen, A. M.; van Leusen, D. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995, Vol. 5, p 3650. ten Have, R.; Leusink, F. R.; van Leusen, A. M. Synthesis 1996, 871. For an exhaustive account, see: (J) van Leusen, D.; van Leusen, A. M. Org. React, in press.
11. Some references are as follows: (a) Possel, O.; van Leusen, A. M. Heterocycles 1977, 7, 77. (b) Moskal, J.; van Leusen, A. M. J. Org. Chem. 1986, 51, 4131. Magnus, P.; Gallagher, T.; Schultz, J.; Or, Y.-S.; Ananthanarayan, T. P. J. Am. Chem. Soc. 1987, 109, 2706. (d) van Leusen, D.; Flentge, E.; van Leusen, A. M. Tetrahedron 1991, 47, 4639. (e) van Leusen, D.; van Echten, E.; van Leusen, A. M. J. Org. Chem. 1992, 57, 2245. (f) Dell'Erba, C.; Giglio, A.; Mugnoli, A.; Novi, M.; Petrillo, G.; Stagnaro, P. Tetrahedron 1995, 51, 5181. (g) van Leusen, A. M.; van Leusen, D. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995; Vol. 7, p 4973. (h) van Leusen, A. M.; van Leusen, D. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995, Vol. 5, p 3650. ten Have, R.; Leusink, F. R.; van Leusen, A. M. Synthesis 1996, 871. For an exhaustive account, see: (J) van Leusen, D.; van Leusen, A. M. Org. React, in press.
12. Some references are as follows: (a) Possel, O.; van Leusen, A. M. Heterocycles 1977, 7, 77. (b) Moskal, J.; van Leusen, A. M. J. Org. Chem. 1986, 51, 4131. Magnus, P.; Gallagher, T.; Schultz, J.; Or, Y.-S.; Ananthanarayan, T. P. J. Am. Chem. Soc. 1987, 109, 2706. (d) van Leusen, D.; Flentge, E.; van Leusen, A. M. Tetrahedron 1991, 47, 4639. (e) van Leusen, D.; van Echten, E.; van Leusen, A. M. J. Org. Chem. 1992, 57, 2245. (f) Dell'Erba, C.; Giglio, A.; Mugnoli, A.; Novi, M.; Petrillo, G.; Stagnaro, P. Tetrahedron 1995, 51, 5181. (g) van Leusen, A. M.; van Leusen, D. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995; Vol. 7, p 4973. (h) van Leusen, A. M.; van Leusen, D. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995, Vol. 5, p 3650. ten Have, R.; Leusink, F. R.; van Leusen, A. M. Synthesis 1996, 871. For an exhaustive account, see: (J) van Leusen, D.; van Leusen, A. M. Org. React, in press.
13. Some references are as follows: (a) Possel, O.; van Leusen, A. M. Heterocycles 1977, 7, 77. (b) Moskal, J.; van Leusen, A. M. J. Org. Chem. 1986, 51, 4131. Magnus, P.; Gallagher, T.; Schultz, J.; Or, Y.-S.; Ananthanarayan, T. P. J. Am. Chem. Soc. 1987, 109, 2706. (d) van Leusen, D.; Flentge, E.; van Leusen, A. M. Tetrahedron 1991, 47, 4639. (e) van Leusen, D.; van Echten, E.; van Leusen, A. M. J. Org. Chem. 1992, 57, 2245. (f) Dell'Erba, C.; Giglio, A.; Mugnoli, A.; Novi, M.; Petrillo, G.; Stagnaro, P. Tetrahedron 1995, 51, 5181. (g) van Leusen, A. M.; van Leusen, D. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995; Vol. 7, p 4973. (h) van Leusen, A. M.; van Leusen, D. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995, Vol. 5, p 3650. ten Have, R.; Leusink, F. R.; van Leusen, A. M. Synthesis 1996, 871. For an exhaustive account, see: (J) van Leusen, D.; van Leusen, A. M. Org. React, in press.
14. Some references are as follows: (a) Possel, O.; van Leusen, A. M. Heterocycles 1977, 7, 77. (b) Moskal, J.; van Leusen, A. M. J. Org. Chem. 1986, 51, 4131. Magnus, P.; Gallagher, T.; Schultz, J.; Or, Y.-S.; Ananthanarayan, T. P. J. Am. Chem. Soc. 1987, 109, 2706. (d) van Leusen, D.; Flentge, E.; van Leusen, A. M. Tetrahedron 1991, 47, 4639. (e) van Leusen, D.; van Echten, E.; van Leusen, A. M. J. Org. Chem. 1992, 57, 2245. (f) Dell'Erba, C.; Giglio, A.; Mugnoli, A.; Novi, M.; Petrillo, G.; Stagnaro, P. Tetrahedron 1995, 51, 5181. (g) van Leusen, A. M.; van Leusen, D. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995; Vol. 7, p 4973. (h) van Leusen, A. M.; van Leusen, D. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995, Vol. 5, p 3650. ten Have, R.; Leusink, F. R.; van Leusen, A. M. Synthesis 1996, 871. For an exhaustive account, see: (J) van Leusen, D.; van Leusen, A. M. Org. React, in press.
15. Some references are as follows: (a) Possel, O.; van Leusen, A. M. Heterocycles 1977, 7, 77. (b) Moskal, J.; van Leusen, A. M. J. Org. Chem. 1986, 51, 4131. Magnus, P.; Gallagher, T.; Schultz, J.; Or, Y.-S.; Ananthanarayan, T. P. J. Am. Chem. Soc. 1987, 109, 2706. (d) van Leusen, D.; Flentge, E.; van Leusen, A. M. Tetrahedron 1991, 47, 4639. (e) van Leusen, D.; van Echten, E.; van Leusen, A. M. J. Org. Chem. 1992, 57, 2245. (f) Dell'Erba, C.; Giglio, A.; Mugnoli, A.; Novi, M.; Petrillo, G.; Stagnaro, P. Tetrahedron 1995, 51, 5181. (g) van Leusen, A. M.; van Leusen, D. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995; Vol. 7, p 4973. (h) van Leusen, A. M.; van Leusen, D. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995, Vol. 5, p 3650. ten Have, R.; Leusink, F. R.; van Leusen, A. M. Synthesis 1996, 871. For an exhaustive account, see: (J) van Leusen, D.; van Leusen, A. M. Org. React, in press.
16. The first stannylated pyrrole, 1-(dimethylamino)-2-(trimethylstannyl)pyrrole, was reported in 1981: Martinez, G. R.; Grieco, P. A.; Srinivasan, C. V. J. Org. Chem. 1981, 46, 3760. The first application in a Stille cross-coupling (of 1-methyl-2-(trimethylstannyl)pyrrole) dates from 1986: Bailey, T. R. Tetrahedron Lett. 1986, 27, 4407.
17. The first stannylated pyrrole, 1-(dimethylamino)-2-(trimethylstannyl)pyrrole, was reported in 1981: Martinez, G. R.; Grieco, P. A.; Srinivasan, C. V. J. Org. Chem. 1981, 46, 3760. The first application in a Stille cross-coupling (of 1-methyl-2-(trimethylstannyl)pyrrole) dates from 1986: Bailey, T. R. Tetrahedron Lett. 1986, 27, 4407.
18. Alvarez, A.; Guzman, A.; Ruiz, A.; Velarde, E.; Muchowski, J. M. J. Org. Chem. 1992, 57, 1653.
19. Leading references: Zerbi, G.; Veronelli, M.; Martina, S.; Schlüter, A.-D.; Wegner, G. Adv. Mater. 1994, 6, 315. Groenendaal, L.; Peerlings, H. W. I.; Havinga, E. E.; Vekemans, J. A. J. M.; Meijer, E. W. Synth. Metals 1995, 69, 467.
20. Leading references: Zerbi, G.; Veronelli, M.; Martina, S.; Schlüter, A.-D.; Wegner, G. Adv. Mater. 1994, 6, 315. Groenendaal, L.; Peerlings, H. W. I.; Havinga, E. E.; Vekemans, J. A. J. M.; Meijer, E. W. Synth. Metals 1995, 69, 467.
21. Groenendaal, L. Ph.D. Thesis, Eindhoven (The Netherlands), 1996.
22. Wang, J.; Scott, A. I. Tetrahedron Lett. 1996, 37, 3247.
23. van Nispen, S. P. J.; Mensink, C.; van Leusen, A. M. Tetrahedron Lett. 1980, 21, 3723.
24. The X-ray structure of the N-Boc derivative of 3a was published elsewhere: Meetsma, A.; Dijkstra, H. P.; ten Have, R.; van Leusen, A. M. Acta Crystallogr. 1996, C52, 2747. This paper, which also describes the nonoptimized synthesis of 3a and its N-Boc derivative, is to be considered the preliminary of the present paper.
25. Houwing, H. A.; van Leusen, A. M. J. Heterocycl. Chem. 1981, 18, 1127, and ref 5h. Furthermore, for the use of Pd, Pt, and W complexes of isocyanides, see: Fehlhammer, W. P.; Bartel, K.; Völkl, A.; Achatz, D Z. Naturforsch. 1982, 37b, 1044.
26. Houwing, H. A.; van Leusen, A. M. J. Heterocycl. Chem. 1981, 18, 1127, and ref 5h. Furthermore, for the use of Pd, Pt, and W complexes of isocyanides, see: Fehlhammer, W. P.; Bartel, K.; Völkl, A.; Achatz, D Z. Naturforsch. 1982, 37b, 1044.
27. 4 may be seen as an indication that the Stille reaction of N-unprotected pyrroles ought to be possible too.
28. Fuson, T. C.; Thomas, N. J. Org. Chem. 1953, 18, 1762.
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