Palladium(0)-catalyzed carbonylation-coupling-cyclization of allenic sulfonamides with aryl iodides and carbon monoxide

Organic Letters

Volumn 3, Issue 4, 2001, Pages 511-514

  Kang, Suk Ku ^a   Kim, Kwang Jin ^a  

^a Sungkyunkwan University   (South Korea)

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ARTICLE;

EID: 0001417393     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006796o     Document Type: Article

References (23)

1. Review: Zimmer, R.; Dinesh, C. U.; Nandanan, E.; Khan, F. A. Chem. Rev. 2000, 100, 3257-3282.
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3. (b) Davis, I. W.; Scopes, D. I. C.; Gallagher, T. Synlett 1993, 85-87.
4. (c) Karstens, W. F. J.; Rutjes, F. P. J. T.; Hiemstra, H. Tetrahedron Lett. 1997, 38, 6275-6278.
5. (d) Karstens, W. F. J.; Stol, M.; Rutjes, F. P. J. T.; Hiemstra, H. Synlett 1998, 1126-1128.
6. (e) Prasad, J. S.; Liebeskind, L. S. Tetrahedron Lett. 1988, 29, 425 7-4260.
7. (f) Ohno, H.; Toda, A.; Miwa, Y.; Taga, T.; Osawa, E.; Yamaoka, Y.; Fujii, N.; Ibuka, T. J. Org. Chem. 1999, 64, 2992-2993.
8. (g) Rutjes, F. P. J. T.; Tjen, K. C. M. F.; Wolf, L. B.; Karstens, W. F. J.; Schoemaker, H. E.; Hiemstra, H. Org. Lett. 1999, 1, 717-720.
9. (h) Anzai, M.; Toda, A.; Ohno, H.; Takemoto, Y.; Fujii, N.; Ibuka, T. Tetrahedron Lett. 1999, 40, 7393-7397.
10. (I) Kang, S.-K.; Baik, T.-G.; Kulak, A. N. Synlett 1999, 324-326.
11. The palladium-catalyzed methoxycarbonylation of allene-substituted amines to form pyrrolidine or piperidine carboxylic esters was known by Gallagher et al. See: (a) Gallagher, T.; Davies, I. W.; Jones, S. W.; Lathbury, D.; Mahon, M. F.; Molloy, K. C.; Shaw, R. W.; Vernon, P. J. Chem. Soc., Perkin Trans. 1 1992, 433-440.
12. (b) Fox, D. N. A.; Gallagher, T. Tetrahedron 1990, 46, 4697-4710.
13. (c) Fox, D. N. A.; Lathbury, D.; Mahon, M. F.; Molloy, K. C.; Gallagher, T. J. Am. Chem. Soc. 1991, 113, 2652-2656.
14. (e) Lathbury, D.; Vernon, P.; Gallagher, T. Tetrahedron Lett. 1986, 27, 6009-6012.
15. Bates, R. W.; Rama-Devi, T.; Ko, H.-H. Tetrahedron 1995, 51, 12939-12954.
16. The palladium(0)-catalyzed cyclization - carbonylation - coupling of aryl halides and γ-hydroxyallenes to form aryl(tetrafuran-2-yl)vinyl ketones is known. See: Walkup, R. D.; Guan, L.; Kim, Y. S.; Kim, S. W. Tetrahedron Lett. 1995, 36, 3805-3808.
17. The α-allenic p-toluenesulfonamide 1a was prepared from deca-1,2-diene-4-ol by Mitsunobu reaction followed by deprotection and tosylation in 52% yield. matrix presented
18. 3CN for 18 h gave 3a and 4a in 42% yield. As the solvent, DMF can be used to ovtain the similar products and yields.
19. 2 column chromatography (hexanes/EtOAc, 6:1) to give 3-pyrroline 3a (32 mg, 24%) and 2-pyrroline 4a (76 mg, 57%). Walkup et al. suggested two possible mechanisms for cyclization-coupling between aryl halides and γ-hydroxyallenes (ref 4).
20. 3-allylpalladium(II) complex is considered to be operative for intermolecular coupling nucleophilic reaction with amines. See: (a) Shimizu, I.; Tsuji, J. Chem. Lett. 1984, 233-236.
21. (b) Cazes, B. Pure Appl. Chem. 1990, 62, 1867-1878.
22. (c) Larock, R. C.; Berrios-Pena, N. G.; Fried, C. A. J. Org. Chem. 1991, 56, 2615-2617. Alper et al. suggested that the initial addition of aroylpalladium to allene is followed by nucleophilic attack of the hydroxy group in the carbonylation of o-iodophenol with allenes. See: Okuro, K.; Alper, H. J. Org. Chem. 1997, 62, 1566-1567.
23. (c) Larock, R. C.; Berrios-Pena, N. G.; Fried, C. A. J. Org. Chem. 1991, 56, 2615-2617. Alper et al. suggested that the initial addition of aroylpalladium to allene is followed by nucleophilic attack of the hydroxy group in the carbonylation of o-iodophenol with allenes. See: Okuro, K.; Alper, H. J. Org. Chem. 1997, 62, 1566-1567.