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Pyrrole syntheses based on the coupling of alkynes and carbene complexes have precedent; however, nitrogen is attached to the carbene in all cases. (a) Merlic, C. A.; Baur, A.; Aldrich, C. A. J. Am. Chem. Soc. 2000, 122, 7398-7399. (b) Parlier, A.; Rudler, M.; Rudler, H.; Goumont, R.; Daran, J. C.; Vaissermann, J. Organometallics 1995, 14, 2760-2774. (c) Grotjahn, D. B.; Kroll, F. E. K.; Schaefer, T.; Harms, K.; Dötz, K. H. Organometallics 1992, 11, 298-310. (d) Aumann, R.; Heinen, H.; Goddard, R.; Krueger, C. Chem. Ber. 1991, 124, 2587-2593. (e) Dragisich, V.; Murray, C. K.; Warner, B. P.; Wulff, W. D.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 1251-1253. (f) Dragisich, V.; Wulff, W. D.; Hoogsteen, K. Organometallics 1990, 9, 2867-2870.
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Pyrrole syntheses based on the coupling of alkynes and carbene complexes have precedent; however, nitrogen is attached to the carbene in all cases. (a) Merlic, C. A.; Baur, A.; Aldrich, C. A. J. Am. Chem. Soc. 2000, 122, 7398-7399. (b) Parlier, A.; Rudler, M.; Rudler, H.; Goumont, R.; Daran, J. C.; Vaissermann, J. Organometallics 1995, 14, 2760-2774. (c) Grotjahn, D. B.; Kroll, F. E. K.; Schaefer, T.; Harms, K.; Dötz, K. H. Organometallics 1992, 11, 298-310. (d) Aumann, R.; Heinen, H.; Goddard, R.; Krueger, C. Chem. Ber. 1991, 124, 2587-2593. (e) Dragisich, V.; Murray, C. K.; Warner, B. P.; Wulff, W. D.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 1251-1253. (f) Dragisich, V.; Wulff, W. D.; Hoogsteen, K. Organometallics 1990, 9, 2867-2870.
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7
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0000731325
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Pyrrole syntheses based on the coupling of alkynes and carbene complexes have precedent; however, nitrogen is attached to the carbene in all cases. (a) Merlic, C. A.; Baur, A.; Aldrich, C. A. J. Am. Chem. Soc. 2000, 122, 7398-7399. (b) Parlier, A.; Rudler, M.; Rudler, H.; Goumont, R.; Daran, J. C.; Vaissermann, J. Organometallics 1995, 14, 2760-2774. (c) Grotjahn, D. B.; Kroll, F. E. K.; Schaefer, T.; Harms, K.; Dötz, K. H. Organometallics 1992, 11, 298-310. (d) Aumann, R.; Heinen, H.; Goddard, R.; Krueger, C. Chem. Ber. 1991, 124, 2587-2593. (e) Dragisich, V.; Murray, C. K.; Warner, B. P.; Wulff, W. D.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 1251-1253. (f) Dragisich, V.; Wulff, W. D.; Hoogsteen, K. Organometallics 1990, 9, 2867-2870.
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8
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0006893310
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Pyrrole syntheses based on the coupling of alkynes and carbene complexes have precedent; however, nitrogen is attached to the carbene in all cases. (a) Merlic, C. A.; Baur, A.; Aldrich, C. A. J. Am. Chem. Soc. 2000, 122, 7398-7399. (b) Parlier, A.; Rudler, M.; Rudler, H.; Goumont, R.; Daran, J. C.; Vaissermann, J. Organometallics 1995, 14, 2760-2774. (c) Grotjahn, D. B.; Kroll, F. E. K.; Schaefer, T.; Harms, K.; Dötz, K. H. Organometallics 1992, 11, 298-310. (d) Aumann, R.; Heinen, H.; Goddard, R.; Krueger, C. Chem. Ber. 1991, 124, 2587-2593. (e) Dragisich, V.; Murray, C. K.; Warner, B. P.; Wulff, W. D.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 1251-1253. (f) Dragisich, V.; Wulff, W. D.; Hoogsteen, K. Organometallics 1990, 9, 2867-2870.
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Aumann, R.1
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9
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0025220488
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Pyrrole syntheses based on the coupling of alkynes and carbene complexes have precedent; however, nitrogen is attached to the carbene in all cases. (a) Merlic, C. A.; Baur, A.; Aldrich, C. A. J. Am. Chem. Soc. 2000, 122, 7398-7399. (b) Parlier, A.; Rudler, M.; Rudler, H.; Goumont, R.; Daran, J. C.; Vaissermann, J. Organometallics 1995, 14, 2760-2774. (c) Grotjahn, D. B.; Kroll, F. E. K.; Schaefer, T.; Harms, K.; Dötz, K. H. Organometallics 1992, 11, 298-310. (d) Aumann, R.; Heinen, H.; Goddard, R.; Krueger, C. Chem. Ber. 1991, 124, 2587-2593. (e) Dragisich, V.; Murray, C. K.; Warner, B. P.; Wulff, W. D.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 1251-1253. (f) Dragisich, V.; Wulff, W. D.; Hoogsteen, K. Organometallics 1990, 9, 2867-2870.
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0006938283
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Pyrrole syntheses based on the coupling of alkynes and carbene complexes have precedent; however, nitrogen is attached to the carbene in all cases. (a) Merlic, C. A.; Baur, A.; Aldrich, C. A. J. Am. Chem. Soc. 2000, 122, 7398-7399. (b) Parlier, A.; Rudler, M.; Rudler, H.; Goumont, R.; Daran, J. C.; Vaissermann, J. Organometallics 1995, 14, 2760-2774. (c) Grotjahn, D. B.; Kroll, F. E. K.; Schaefer, T.; Harms, K.; Dötz, K. H. Organometallics 1992, 11, 298-310. (d) Aumann, R.; Heinen, H.; Goddard, R.; Krueger, C. Chem. Ber. 1991, 124, 2587-2593. (e) Dragisich, V.; Murray, C. K.; Warner, B. P.; Wulff, W. D.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 1251-1253. (f) Dragisich, V.; Wulff, W. D.; Hoogsteen, K. Organometallics 1990, 9, 2867-2870.
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This stereochemistry is generally obtained in chromium carbene-alkyne couplings. McCallum, J. S.; Kunng, F. A.; Gilbertson, S. A.; Wulff, W. D. Organometallics 1988, 7, 2346-2360.
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(a) Barluenga, J.; Tomas, M.; Rubio, E.; Lopaz-Peligrino, J. A.; Garcia-Granda, S.; Priede, M. P. J. Am. Chem. Soc. 1999, 121, 3065-3071.
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the reaction under study in this manuscript affords pyrroles as minor products
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(b) Barluenga, J.; Ballesteros, A.; Santamaria, J.; Tomas, M. J. Organomet. Chem. 2002, 643-644, 363-368; the reaction under study in this manuscript affords pyrroles as minor products.
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Recent examples: (a) Gadaginamath, G. S.; Shyadligeri, A. S. Indian J. Chem. B 2000, 39B, 31-35. (b) Al-Ashmawy, M. I.; El-Samii, Z. K. A.; El Feky, S. A.; Osman, N. A. Boll. Chim. Farm. 1998, 137, 110-114. (c) Hiremath, U. S.; Yelamaggad, C. V.; Badami, B. V.; Puranik, G. S. J. Chem. Res., Synop. 1994, 502-503. (d) Jacobi, P. A.; Cai, G. Heterocycles 1993, 35, 1103-1120.
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Recent examples: (a) Gadaginamath, G. S.; Shyadligeri, A. S. Indian J. Chem. B 2000, 39B, 31-35. (b) Al-Ashmawy, M. I.; El-Samii, Z. K. A.; El Feky, S. A.; Osman, N. A. Boll. Chim. Farm. 1998, 137, 110-114. (c) Hiremath, U. S.; Yelamaggad, C. V.; Badami, B. V.; Puranik, G. S. J. Chem. Res., Synop. 1994, 502-503. (d) Jacobi, P. A.; Cai, G. Heterocycles 1993, 35, 1103-1120.
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Recent examples: (a) Gadaginamath, G. S.; Shyadligeri, A. S. Indian J. Chem. B 2000, 39B, 31-35. (b) Al-Ashmawy, M. I.; El-Samii, Z. K. A.; El Feky, S. A.; Osman, N. A. Boll. Chim. Farm. 1998, 137, 110-114. (c) Hiremath, U. S.; Yelamaggad, C. V.; Badami, B. V.; Puranik, G. S. J. Chem. Res., Synop. 1994, 502-503. (d) Jacobi, P. A.; Cai, G. Heterocycles 1993, 35, 1103-1120.
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Recent examples: (a) Attanasi, O. A.; De Crescentini, L.; Filippone, P.; Fringuelli, F.; Mantellini, F.; Matteucci, M.; Piermatti, O.; Pizzo, F. Helv. Chim. Acta 2001, 84, 513-525. (b) Attanasi, O. A.; De Crescentini, L.; Filippone, P.; Mantellini, F.; Tietze, L. F. Tetrahedron 2001, 57, 5855-5863. (c) Attanasi, O. A.; Filippone, P.; Perrulli, F. R.; Santeusanio, S. Tetrahedron 2001, 57, 1387-1394. (d) Attanasi, O. A.; De Crescentini, L.; Filippone, P.; Mantellini, F. Synlett 2000, 955-958.
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35
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Recent examples: (a) Attanasi, O. A.; De Crescentini, L.; Filippone, P.; Fringuelli, F.; Mantellini, F.; Matteucci, M.; Piermatti, O.; Pizzo, F. Helv. Chim. Acta 2001, 84, 513-525. (b) Attanasi, O. A.; De Crescentini, L.; Filippone, P.; Mantellini, F.; Tietze, L. F. Tetrahedron 2001, 57, 5855-5863. (c) Attanasi, O. A.; Filippone, P.; Perrulli, F. R.; Santeusanio, S. Tetrahedron 2001, 57, 1387-1394. (d) Attanasi, O. A.; De Crescentini, L.; Filippone, P.; Mantellini, F. Synlett 2000, 955-958.
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Tietze, L.F.5
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36
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0035843385
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Recent examples: (a) Attanasi, O. A.; De Crescentini, L.; Filippone, P.; Fringuelli, F.; Mantellini, F.; Matteucci, M.; Piermatti, O.; Pizzo, F. Helv. Chim. Acta 2001, 84, 513-525. (b) Attanasi, O. A.; De Crescentini, L.; Filippone, P.; Mantellini, F.; Tietze, L. F. Tetrahedron 2001, 57, 5855-5863. (c) Attanasi, O. A.; Filippone, P.; Perrulli, F. R.; Santeusanio, S. Tetrahedron 2001, 57, 1387-1394. (d) Attanasi, O. A.; De Crescentini, L.; Filippone, P.; Mantellini, F. Synlett 2000, 955-958.
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Santeusanio, S.4
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37
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0033944316
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Recent examples: (a) Attanasi, O. A.; De Crescentini, L.; Filippone, P.; Fringuelli, F.; Mantellini, F.; Matteucci, M.; Piermatti, O.; Pizzo, F. Helv. Chim. Acta 2001, 84, 513-525. (b) Attanasi, O. A.; De Crescentini, L.; Filippone, P.; Mantellini, F.; Tietze, L. F. Tetrahedron 2001, 57, 5855-5863. (c) Attanasi, O. A.; Filippone, P.; Perrulli, F. R.; Santeusanio, S. Tetrahedron 2001, 57, 1387-1394. (d) Attanasi, O. A.; De Crescentini, L.; Filippone, P.; Mantellini, F. Synlett 2000, 955-958.
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Synlett
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Attanasi, O.A.1
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40
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(c) Attanasi, O. A.; Filippone, P.; Perrulli, F. R.; Santeusanio, S. Tetrahedron 2001, 57, 1387-1394.
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Santeusanio, S.4
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