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Aryne-isocyanide-aldehyde: (a) Yoshida, H.; Fukushima, H.; Ohshita, J.; Kunai, A. Angew.Chem., Int. Ed. 2004, 43, 3935-3938.
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Aryne-isocyanide-aldehyde: (a) Yoshida, H.; Fukushima, H.; Ohshita, J.; Kunai, A. Angew.Chem., Int. Ed. 2004, 43, 3935-3938.
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Aryne-isocyanideimine: (b) Yoshida, H.; Fukushima, H.; Ohshita, J.; Kunai, A. Tetrahedron Lett. 2004, 45, 8659-8662.
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2: (c) Yoshida, H.; Fukushima, H.; Ohshita, J.; Kunai, A. J. Am. Chem. Soc. 2006, 128, 11040-11041.
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2: (c) Yoshida, H.; Fukushima, H.; Ohshita, J.; Kunai, A. J. Am. Chem. Soc. 2006, 128, 11040-11041.
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See also: (d) Yoshida, H.; Fukushima, H.; Morishita, T.; Ohshita, J.; Kunai, A. Tetrahedron 2007, 63, 4793-4805.
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Formation of monosubstituted arenes by proton abstraction: (a) Sato, Y.; Toyooka, T.; Aoyama, T.; Shirai, H. J. Org. Chem. 1976, 41, 3559-3564.
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Formation of monosubstituted arenes by proton abstraction: (a) Sato, Y.; Toyooka, T.; Aoyama, T.; Shirai, H. J. Org. Chem. 1976, 41, 3559-3564.
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For a review on insertion reactions of arynes into element-element σ-bond, see
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For a review on insertion reactions of arynes into element-element σ-bond, see: Peña, D.; Pérez, D.; Guitián, E. Angew. Chem., Int. Ed. 2006, 45, 3578-3581.
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(p) Yoshida, H.; Mimura, Y.; Ohshita, J.; Kunai, A. Chem. Commun. 2007, 2405-2407.
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Other three-component couplings using neutral nucleophiles: (a) Yoshida, H.; Watanabe, M.; Fukushima, H.; Ohshita, J.; Kunai, A. Org. Lett. 2004, 6, 4049-4051.
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The reaction of arynes with primary and secondary amines: (a) Snieckus, V. Chem. Rev. 1990, 90, 879-933.
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(b) Wickham, P. P.; Hazen, K. H.; Guo, H.; Jones, G.; Reuter, K. H.; Scott, W. J. J. Org. Chem. 1991, 56, 2045-2050.
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38
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48249094862
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The reaction of benzyne with benzaldehyde was reported to produce 2-(dimethylamino)benzhydrol (12% yield), whose dimethylamino moiety was derived from a benzyne precursor (1-(2-carboxyphenyl)-3,3-dimethyltriazene). However, this reaction was not developed as a useful synthetic procedure, because it required harsh conditions (160°C) and excess aldehyde (∼39 equiv). Nakayama, J.; Yoshida, M.; Shimamura, O. Chem. Lett. 1973, 451-454.
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The reaction of benzyne with benzaldehyde was reported to produce 2-(dimethylamino)benzhydrol (12% yield), whose dimethylamino moiety was derived from a benzyne precursor (1-(2-carboxyphenyl)-3,3-dimethyltriazene). However, this reaction was not developed as a useful synthetic procedure, because it required harsh conditions (160°C) and excess aldehyde (∼39 equiv). Nakayama, J.; Yoshida, M.; Shimamura, O. Chem. Lett. 1973, 451-454.
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39
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33845560452
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Similar products can be synthesized by the direct ortho-lithiation of anilides followed by reaction with an electrophile, although the highly basic reaction conditions would limit the use of substrates bearing relatively sensitive functional groups, a Fuhrer, W, and Gschwend, H. W. J. Org. Chem. 1979, 44, 1133-1136
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Similar products can be synthesized by the direct ortho-lithiation of anilides followed by reaction with an electrophile, although the highly basic reaction conditions would limit the use of substrates bearing relatively sensitive functional groups. (a) Fuhrer, W.; and Gschwend, H. W. J. Org. Chem. 1979, 44, 1133-1136.
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34548187748
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48249152880
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The TMS group in aminosilylated product 8 was demonstrated to derive not from 1 but from 2a. See ref 3i
-
The TMS group in aminosilylated product 8 was demonstrated to derive not from 1 but from 2a. See ref 3i.
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44
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0348041998
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A large amount of N,N-diethylaniline was formed as a byproduct in this reaction, which demonstrates an advantage of the use of aminosilanes in the three-component coupling. The existence of only a catalytic amount of amines, generated from aminosilanes and benzoic acid, in the reaction mixture would decrease aniline derivatives. For N-arylation of amines by the use of arynes, see: (a) Liu, Z.; Larock, R. C. Org. Lett. 2003, 5, 4673-4675.
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A large amount of N,N-diethylaniline was formed as a byproduct in this reaction, which demonstrates an advantage of the use of aminosilanes in the three-component coupling. The existence of only a catalytic amount of amines, generated from aminosilanes and benzoic acid, in the reaction mixture would decrease aniline derivatives. For N-arylation of amines by the use of arynes, see: (a) Liu, Z.; Larock, R. C. Org. Lett. 2003, 5, 4673-4675.
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An amine and a silyl carboxylate are readily formed in the reaction of an aminosilane and a carboxylic acid: (a) Wissner, A. Tetrahedron Lett. 1978, 19, 2749-2752
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An amine and a silyl carboxylate are readily formed in the reaction of an aminosilane and a carboxylic acid: (a) Wissner, A. Tetrahedron Lett. 1978, 19, 2749-2752.
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(b) Ruhlmann, K. Chem. Ber. 1961, 94, 1876-1878.
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Ruhlmann, K.1
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48249113194
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A reviewer pointed out that there may be an attractive hydrogen bonding between the amine H in 11 and an electrophile, which enhances the electrophilicity of 3 or 6.
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A reviewer pointed out that there may be an attractive hydrogen bonding between the amine H in 11 and an electrophile, which enhances the electrophilicity of 3 or 6.
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49
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33645012569
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Various alcohols are readily transformed into the respective silyl ethers via action with aminosilanes: (a) Shirini, F, Mollarazi, E. Synth. Commun. 2006, 36, 1109-1115
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Various alcohols are readily transformed into the respective silyl ethers via action with aminosilanes: (a) Shirini, F.; Mollarazi, E. Synth. Commun. 2006, 36, 1109-1115.
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50
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(b) Gautret, P.; El-Ghammarti, S.; Legrand, A.; Couturier, D.; Rigo, B. Synth. Commun. 1996, 26, 707-717.
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51
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48249139704
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Because there was an excess of fluoride in the reaction mixture, three-component coupling products would exist as silicates, amides or alkoxides before a workup process. Therefore, we could only detect trace amounts of silyl ether 12 or silylamine 13 in crude products. For protodesilylation of silyl ethers with a fluoride ion, see: Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley & Sons: New York, 1999; Chapter 2, pp 113-148.
-
Because there was an excess of fluoride in the reaction mixture, three-component coupling products would exist as silicates, amides or alkoxides before a workup process. Therefore, we could only detect trace amounts of silyl ether 12 or silylamine 13 in crude products. For protodesilylation of silyl ethers with a fluoride ion, see: Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley & Sons: New York, 1999; Chapter 2, pp 113-148.
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52
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Preferential nucleophilic attack at a para position of a chlorine atom also occurred in electrophilic coupling reactions of 4-chlorobenzyne: (a) Bunnett, J. F, Pyun, C. J. Org. Chem. 1969, 34, 2035-2037
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Preferential nucleophilic attack at a para position of a chlorine atom also occurred in electrophilic coupling reactions of 4-chlorobenzyne: (a) Bunnett, J. F.; Pyun, C. J. Org. Chem. 1969, 34, 2035-2037.
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54
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