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. 2005 Oct 14;70(21):8638-41.
doi: 10.1021/jo051450i.

Palladium-catalyzed synthesis of N-vinyl pyrroles and indoles

Affiliations

Palladium-catalyzed synthesis of N-vinyl pyrroles and indoles

Mohammad Movassaghi et al. J Org Chem. .

Abstract

A stereospecific palladium-catalyzed N-vinylation of azaheterocycles with vinyl triflates is described. Cyclic and acyclic vinyl triflates along with nonnucleophilic azaheterocycles were found to be substrates for this palladium-catalyzed synthesis of N-vinyl pyrrole and indole derivatives.

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Figures

SCHEME 1
SCHEME 1
Stereospecific synthesis of β-pyrrolyl enoates.
CHART 1
CHART 1

References

    1. Wolfe JP, Wagaw S, Marcoux JF, Buchwald SL. Acc Chem Res. 1998;31:805–818.
    2. Hartwig JF. Acc Chem Res. 1998;31:852–860.
    3. Hartwig JF. Angew Chem, Int Ed. 1998;37:2046–2067. - PubMed
    4. Yang BH, Buchwald SL. J Organomet Chem. 1999;576:125–146.
    5. Muci AR, Buchwald SL. Top Curr Chem. 2002;219:131–209.
    6. Hartwig JF. In: Handbook of Organopalladium Chemistry for Organic Synthesis. Negishi E, editor. Wiley-Interscience; New York: 2002. p. 1051.
    1. Wolfe JP, Wagaw S, Buchwald SL. J Am Chem Soc. 1996;118:7215–7216.
    2. Driver MS, Hartwig JF. J Am Chem Soc. 1996;118:7217–7218.
    3. For examples of palladium catalyzed N-arylation of azoles, see:

    4. Mann G, Hartwig JF, Driver MS, Fernández-Rivas C. J Am Chem Soc. 1998;120:827–828.
    5. Old DW, Harris MC, Buchwald SL. Org Lett. 2000;2:1403–1406. - PubMed
    6. Watanabe M, Nishiyama M, Yamamoto T, Koie Y. Tetrahedron Lett. 2000;41:481–483.
    1. For examples of copper-catalyzed N-arylation, see:

    2. Kiyomori A, Marcoux JF, Buchwald SL. Tetrahedron Lett. 1999;40:2657–2660.
    3. Collman JP, Zhong M. Org Lett. 2000;2:1233–1236. - PubMed
    4. Gujadhur RK, Bates CG, Venkataraman D. Org Lett. 2001;3:4315–4317. - PubMed
    5. Klapars A, Antilla JC, Huang X, Buchwald SL. J Am Chem Soc. 2001;123:7727–7729. - PubMed
    6. Klapars A, Huang X, Buchwald SL. J Am Chem Soc. 2002;124:7421–7428. - PubMed
    7. Kwong FY, Buchwald SL. Org Lett. 2003;5:793–796. - PubMed
    8. Ma D, Cai Q, Zhang H. Org Lett. 2003;5:2453–2455. - PubMed
    9. Padwa A, Crawford KR, Rashatasakhon P, Rose M. J Org Chem. 2003;68:2609–2617. - PubMed
    10. Antilla JC, Baskin JM, Barder TE, Buchwald SL. J Org Chem. 2004;69:5578–5587. - PubMed
    1. For intramolecular palladium catalyzed N-vinylation of amides, see:

    2. Palomo C, Aizpurua JM, Legido M, Picard JP, Dunogues J, Constantieux T. Tetrahedron Lett. 1992;33:3903–3906.
    3. Cuevas J-c, Patil P, Snieckus V. Tetrahedron Lett. 1989;30:5841–5844.
    4. Kozawa Y, Mori M. Tetrahedron Lett. 2002;43:111–114.
    5. For recent reports on palladium catalyzed N-vinylation, see:

    6. Wallace DJ, Klauber DJ, Chen C-y, Volante RP. Org Lett. 2003;5:4749–4752. - PubMed
    7. Klapars A, Campos KR, Chen C-y, Volante RP. Org Lett. 2005;7:1185–1188. - PubMed
    1. For a recent review on the use of copper in cross-coupling reaction, see:

    2. Beletskaya IP, Cheprakov AV. Coordin Chem Rev. 2004;248:2337–2364.
    3. For amidation of vinyl halides with copper as the catalyst or promoter, see:

    4. Ogawa T, Kiji T, Hayami K, Suzuki H. Chem Lett. 1991:1443–1446.
    5. Shen R, Porco JA., Jr Org Lett. 2000;2:1333–1336. - PubMed
    6. Shen R, Lin CT, Porco JA., Jr J Am Chem Soc. 2002;124:5650–5651. - PubMed
    7. Jiang L, Job GE, Klapars A, Buchwald SL. Org Lett. 2003;5:3667–3669. - PubMed
    8. Han C, Shen R, Su S, Porco JA., Jr Org Lett. 2004;6:27–30. - PubMed
    9. Pan X, Cai Q, Ma D. Org Lett. 2004;6:1809–1812. - PubMed
    10. Hu T, Li C. Org Lett. 2005;7:2035–2038. - PubMed
    11. For copper catalyzed and promoted N-alkynylation, respectively, see:

    12. Frederick MO, Mulder JA, Tracey MR, Hsung RP, Huang J, Kurtz KCM, Shen L, Douglas CJ. J Am Chem Soc. 2003;125:2368–2369. - PubMed
    13. Dunetz JR, Danheiser RL. Org Lett. 2003;5:4011–4014. - PMC - PubMed
    14. For a copper catalyzed C–N bond formation using allenyl halides, see:

    15. Trost BM, Stiles DT. Org Lett. 2005;7:2117–2120. - PubMed

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