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23744454427
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Murahashi, S.-I. Ed, Thieme, Stuttgart
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Suginome, M.; Ito, Y. In Science of Synthesis; Murahashi, S.-I. Ed.; Thieme, Stuttgart, 2004, Vol. 19; pp. 445-530.
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Suginome, M.1
Ito, Y.2
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2
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0034665244
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For recent reviews, see
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0000044570
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(a) Niznic, G. E.; Morrison, W. H.; Walborsky, H. M. J. Org. Chem. 1974, 39, 600.
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(b) Murakami, M.; Ito, H.; Ito, Y. J. Org. Chem. 1988, 53, 4158.
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Murakami, M.1
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8
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0000402423
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Reversible addition of weak nucleophiles to isocyanides has been proposed in the intramolecular cyclization of 2-alkynylisocyanobenzenes: Suginome, M, Fukuda, T, Ito, Y. Org. Lett. 1999, 1, 1977
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Reversible addition of weak nucleophiles to isocyanides has been proposed in the intramolecular cyclization of 2-alkynylisocyanobenzenes: Suginome, M.; Fukuda, T.; Ito, Y. Org. Lett. 1999, 1, 1977.
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9
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0000863229
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B: Jacobsen, H.; Berke, H.; Doring, S.; Kehr, G.; Erker, G.; Frohlich, R.; Mayer, O. Organometallics 1999, 18, 1724.
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B: Jacobsen, H.; Berke, H.; Doring, S.; Kehr, G.; Erker, G.; Frohlich, R.; Mayer, O. Organometallics 1999, 18, 1724.
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10
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0000263012
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Al: Fisher, J. D.; Wei, M.-Y.; Willett, R.; Shapiro, P. J. Organometallics 1994, 13, 3324.
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Al: Fisher, J. D.; Wei, M.-Y.; Willett, R.; Shapiro, P. J. Organometallics 1994, 13, 3324.
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11
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0040417141
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Zr: Brackemeyer, T.; Erker, G.; Frohlich, R. Organometallics 1997, 16, 531.
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Zr: Brackemeyer, T.; Erker, G.; Frohlich, R. Organometallics 1997, 16, 531.
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12
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0000773754
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Ti: Carofiglio, T.; Floriani, C.; Chiesi-Villa, A.; Guastini, C. Inorg. Chem.1989, 28, 4417.
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Ti: Carofiglio, T.; Floriani, C.; Chiesi-Villa, A.; Guastini, C. Inorg. Chem.1989, 28, 4417.
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13
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0038541773
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For recent examples of Lewis acid-promoted reactions of isocyanides, see;
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For recent examples of Lewis acid-promoted reactions of isocyanides, see; Chatani, N.; Oshita, M.; Tobisu, M.; Ishii, Y.; Murai, S. J. Am. Chem. Soc. 2003, 125, 7812.
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J. Am. Chem. Soc
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Chatani, N.1
Oshita, M.2
Tobisu, M.3
Ishii, Y.4
Murai, S.5
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15
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12944307854
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Oshita, M.; Yamashita, K.; Tobisu, M.; Chatani, N. J. Am. Chem. Soc. 2005, 127, 761.
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Oshita, M.1
Yamashita, K.2
Tobisu, M.3
Chatani, N.4
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16
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24044476549
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Yoshioka, S.; Oshita, M.; Tobisu, M.; Chatani, N. Org. Lett. 2005, 7, 3697.
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Org. Lett
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Yoshioka, S.1
Oshita, M.2
Tobisu, M.3
Chatani, N.4
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20
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34548159220
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The process is closely related to Vilsmeir-Haack reaction, in which chloroiminium salts work as an electrophile. Jones, G.; Stanforth, S. P. Org. React. 1997, 49, 1.
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The process is closely related to Vilsmeir-Haack reaction, in which chloroiminium salts work as an electrophile. Jones, G.; Stanforth, S. P. Org. React. 1997, 49, 1.
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21
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34548145569
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3), but with reduced yields. For example, the isolated yield of entry 12 in Table 1 was 65%.
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3), but with reduced yields. For example, the isolated yield of entry 12 in Table 1 was 65%.
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22
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34548188740
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4 (24%), HCl (26%), TfOH (51%), and TFA (0%).
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4 (24%), HCl (26%), TfOH (51%), and TFA (0%).
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23
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0346234778
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Tanaka, M.; Sakakura, T.; Tokunaga, Y.; Sodeyama, T. Chem. Lett. 1987, 2373.
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Tanaka, M.1
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Jones, W. D.; Foster, G. P.; Putinas, J. M. J. Am. Chem. Soc. 1987, 109, 5047.
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Jones, W.D.1
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Kobayashi, K.; Matoba, T.; Irisawa, S.; Matsumoto, T.; Morikawa, O.; Konishi, H. Chem. Lett. 1998, 551.
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Xie, W.; Bloomfield, K. M.; Jin, Y.; Dolney, N. Y.; Wang, P. G.Synlett 1999, 498.
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G.Synlett
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28
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0001588270
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Transition metal-mediated insertion of isocyanides into the N-H bond in indoles: Jones, W. D.; Kosar, W. P. J. Am. Chem. Soc. 1986, 108, 5640.
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Transition metal-mediated insertion of isocyanides into the N-H bond in indoles: Jones, W. D.; Kosar, W. P. J. Am. Chem. Soc. 1986, 108, 5640.
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29
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34548149709
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See the Supporting Information for details
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See the Supporting Information for details.
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30
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34548192218
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A crossover experiment indicates that the major part of the proton migration occurs intramolecularly, although an intermolecular process can be operating as a minor path. See Supporting Information for details
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A crossover experiment indicates that the major part of the proton migration occurs intramolecularly, although an intermolecular process can be operating as a minor path. See Supporting Information for details.
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34548187463
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An alternative mechanistic possibility would be the intermediacy of a 3-indolylmetal species, such as D (see below).18 We observed the interaction between indole 1 and GaCl3 by 1H NMR. However, no such interaction was observed when a 1:1 mixture of 1 and 2a was treated with GaCl3, and only the resonance of 2a was shifted. Thus, we currently believe that the dominant species in our reaction is the isocyanide-Lewis acid adduct, as in A, and the insertion proceeds through A
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3, and only the resonance of 2a was shifted. Thus, we currently believe that the dominant species in our reaction is the isocyanide-Lewis acid adduct, as in A, and the insertion proceeds through A.
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0035810401
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Ottoni, O.; de V. F. Neder, A.; Dias, A. K. B.; Cruz, R. P. A.; Aquino, L. B. Org. Lett. 2001, 3, 1005.
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Ottoni, O.1
de, V.F.2
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Dias, A.K.B.4
Cruz, R.P.A.5
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0000566452
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Yuan, Y.; Li, X.; Ding, K. Org. Lett. 2002, 4, 3309.
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Yuan, Y.1
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