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For examples of related carbonylative cyclizations: (a) Colquhoun, H.; Thompson, D. J.; Twigg, M. V. Carbonylation; Plenum Press: New York, 1991. (b) Khumtaveeporn, K.; Alper, H. Acc. Chem. Res. 1995, 28, 414. (c) Tanaka, H.; Abdul Hai, A. K. M.; Sadakane, M.; Okumoto, H.; Torii, S. J. Org. Chem. 1994, 59, 3040. (d) Cho, C. S.; Jiang, L. H.; Shim. S. C. Synth. Commun. 1999, 29, 2695. (e) Van den Hoven, B. G.; Alper, H. J. Am. Chem. Soc. 2001, 123, 10214. (f) Mahadevan, V.; Getzler, Y.; Coates, G. W. Angew. Chem., Int. Ed. 2002, 41, 2781. (g) Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335. (h) Chatani, N.; Kamitani, A.; Murai, S. J. Org. Chem. 2002, 67, 7014.
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For examples of related carbonylative cyclizations: (a) Colquhoun, H.; Thompson, D. J.; Twigg, M. V. Carbonylation; Plenum Press: New York, 1991. (b) Khumtaveeporn, K.; Alper, H. Acc. Chem. Res. 1995, 28, 414. (c) Tanaka, H.; Abdul Hai, A. K. M.; Sadakane, M.; Okumoto, H.; Torii, S. J. Org. Chem. 1994, 59, 3040. (d) Cho, C. S.; Jiang, L. H.; Shim. S. C. Synth. Commun. 1999, 29, 2695. (e) Van den Hoven, B. G.; Alper, H. J. Am. Chem. Soc. 2001, 123, 10214. (f) Mahadevan, V.; Getzler, Y.; Coates, G. W. Angew. Chem., Int. Ed. 2002, 41, 2781. (g) Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335. (h) Chatani, N.; Kamitani, A.; Murai, S. J. Org. Chem. 2002, 67, 7014.
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For examples of related carbonylative cyclizations: (a) Colquhoun, H.; Thompson, D. J.; Twigg, M. V. Carbonylation; Plenum Press: New York, 1991. (b) Khumtaveeporn, K.; Alper, H. Acc. Chem. Res. 1995, 28, 414. (c) Tanaka, H.; Abdul Hai, A. K. M.; Sadakane, M.; Okumoto, H.; Torii, S. J. Org. Chem. 1994, 59, 3040. (d) Cho, C. S.; Jiang, L. H.; Shim. S. C. Synth. Commun. 1999, 29, 2695. (e) Van den Hoven, B. G.; Alper, H. J. Am. Chem. Soc. 2001, 123, 10214. (f) Mahadevan, V.; Getzler, Y.; Coates, G. W. Angew. Chem., Int. Ed. 2002, 41, 2781. (g) Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335. (h) Chatani, N.; Kamitani, A.; Murai, S. J. Org. Chem. 2002, 67, 7014.
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Okumoto, H.4
Torii, S.5
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0000096243
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For examples of related carbonylative cyclizations: (a) Colquhoun, H.; Thompson, D. J.; Twigg, M. V. Carbonylation; Plenum Press: New York, 1991. (b) Khumtaveeporn, K.; Alper, H. Acc. Chem. Res. 1995, 28, 414. (c) Tanaka, H.; Abdul Hai, A. K. M.; Sadakane, M.; Okumoto, H.; Torii, S. J. Org. Chem. 1994, 59, 3040. (d) Cho, C. S.; Jiang, L. H.; Shim. S. C. Synth. Commun. 1999, 29, 2695. (e) Van den Hoven, B. G.; Alper, H. J. Am. Chem. Soc. 2001, 123, 10214. (f) Mahadevan, V.; Getzler, Y.; Coates, G. W. Angew. Chem., Int. Ed. 2002, 41, 2781. (g) Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335. (h) Chatani, N.; Kamitani, A.; Murai, S. J. Org. Chem. 2002, 67, 7014.
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For examples of related carbonylative cyclizations: (a) Colquhoun, H.; Thompson, D. J.; Twigg, M. V. Carbonylation; Plenum Press: New York, 1991. (b) Khumtaveeporn, K.; Alper, H. Acc. Chem. Res. 1995, 28, 414. (c) Tanaka, H.; Abdul Hai, A. K. M.; Sadakane, M.; Okumoto, H.; Torii, S. J. Org. Chem. 1994, 59, 3040. (d) Cho, C. S.; Jiang, L. H.; Shim. S. C. Synth. Commun. 1999, 29, 2695. (e) Van den Hoven, B. G.; Alper, H. J. Am. Chem. Soc. 2001, 123, 10214. (f) Mahadevan, V.; Getzler, Y.; Coates, G. W. Angew. Chem., Int. Ed. 2002, 41, 2781. (g) Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335. (h) Chatani, N.; Kamitani, A.; Murai, S. J. Org. Chem. 2002, 67, 7014.
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For examples of related carbonylative cyclizations: (a) Colquhoun, H.; Thompson, D. J.; Twigg, M. V. Carbonylation; Plenum Press: New York, 1991. (b) Khumtaveeporn, K.; Alper, H. Acc. Chem. Res. 1995, 28, 414. (c) Tanaka, H.; Abdul Hai, A. K. M.; Sadakane, M.; Okumoto, H.; Torii, S. J. Org. Chem. 1994, 59, 3040. (d) Cho, C. S.; Jiang, L. H.; Shim. S. C. Synth. Commun. 1999, 29, 2695. (e) Van den Hoven, B. G.; Alper, H. J. Am. Chem. Soc. 2001, 123, 10214. (f) Mahadevan, V.; Getzler, Y.; Coates, G. W. Angew. Chem., Int. Ed. 2002, 41, 2781. (g) Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335. (h) Chatani, N.; Kamitani, A.; Murai, S. J. Org. Chem. 2002, 67, 7014.
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Mahadevan, V.1
Getzler, Y.2
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0032478977
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For examples of related carbonylative cyclizations: (a) Colquhoun, H.; Thompson, D. J.; Twigg, M. V. Carbonylation; Plenum Press: New York, 1991. (b) Khumtaveeporn, K.; Alper, H. Acc. Chem. Res. 1995, 28, 414. (c) Tanaka, H.; Abdul Hai, A. K. M.; Sadakane, M.; Okumoto, H.; Torii, S. J. Org. Chem. 1994, 59, 3040. (d) Cho, C. S.; Jiang, L. H.; Shim. S. C. Synth. Commun. 1999, 29, 2695. (e) Van den Hoven, B. G.; Alper, H. J. Am. Chem. Soc. 2001, 123, 10214. (f) Mahadevan, V.; Getzler, Y.; Coates, G. W. Angew. Chem., Int. Ed. 2002, 41, 2781. (g) Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335. (h) Chatani, N.; Kamitani, A.; Murai, S. J. Org. Chem. 2002, 67, 7014.
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Chatani, N.1
Morimoto, T.2
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Murai, S.4
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22
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0037020009
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For examples of related carbonylative cyclizations: (a) Colquhoun, H.; Thompson, D. J.; Twigg, M. V. Carbonylation; Plenum Press: New York, 1991. (b) Khumtaveeporn, K.; Alper, H. Acc. Chem. Res. 1995, 28, 414. (c) Tanaka, H.; Abdul Hai, A. K. M.; Sadakane, M.; Okumoto, H.; Torii, S. J. Org. Chem. 1994, 59, 3040. (d) Cho, C. S.; Jiang, L. H.; Shim. S. C. Synth. Commun. 1999, 29, 2695. (e) Van den Hoven, B. G.; Alper, H. J. Am. Chem. Soc. 2001, 123, 10214. (f) Mahadevan, V.; Getzler, Y.; Coates, G. W. Angew. Chem., Int. Ed. 2002, 41, 2781. (g) Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335. (h) Chatani, N.; Kamitani, A.; Murai, S. J. Org. Chem. 2002, 67, 7014.
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J. Org. Chem.
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Chatani, N.1
Kamitani, A.2
Murai, S.3
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23
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0035801522
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(a) Dghaym, R. D.; Dhawan, R.; Arndtsen, B. A. Angew. Chem., Int. Ed. 2001, 40, 3228.
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Angew. Chem., Int. Ed.
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Dghaym, R.D.1
Dhawan, R.2
Arndtsen, B.A.3
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24
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0002789134
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(b) Dghaym, R. D.; Yaccato, K. J.; Arndtsen, B. A. Organometallics 1998, 17, 4.
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Dghaym, R.D.1
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0035912001
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(c) Lafrance, D.; Davis, J. L.; Dhawan, R.; Arndtsen. B. A. Organometallics 2001, 20, 1128.
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Lafrance, D.1
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0344765502
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Kacker, S.; Kim, J. S.; Sen, A. Angew. Chem., Int. Ed. 1998, 37, 1251.
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Kacker, S.1
Kim, J.S.2
Sen, A.3
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27
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0030851133
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This mechanism is similar to those postulated for amidocarbonylation: (a) Beller, M.; Eckert, M.; Vollmuller, F.; Bogdanovic, S.; Geissler, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1494. (b) Beller, M.; Eckert, M. Angew. Chem., Int. Ed. 2000, 39, 1010.
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Beller, M.1
Eckert, M.2
Vollmuller, F.3
Bogdanovic, S.4
Geissler, H.5
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28
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0034677864
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This mechanism is similar to those postulated for amidocarbonylation: (a) Beller, M.; Eckert, M.; Vollmuller, F.; Bogdanovic, S.; Geissler, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1494. (b) Beller, M.; Eckert, M. Angew. Chem., Int. Ed. 2000, 39, 1010.
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Angew. Chem., Int. Ed.
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Beller, M.1
Eckert, M.2
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29
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0013203191
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note
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3.
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30
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0013198654
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note
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Compound 2 is not observed in these reactions, nor are there any major (i.e., >5% yield) identifiable products other than 1.
-
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33
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0013262118
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note
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See the Supporting Information for the synthesis of 1. 4. and 5.
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34
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0013197426
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note
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Side reactions of these N-acyl iminium salts may also inhibit 1 formation; enamides are observed in these reactions in ca. 30% yield.
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