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Volumn 127, Issue 20, 2005, Pages 7474-7479

Facile preparation of various heteroaromatic compounds via azatitanacyclopentadiene intermediates

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; AROMATIC COMPOUNDS; NITRILE RESINS; TITANIUM COMPOUNDS;

EID: 19744370350     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0502730     Document Type: Article
Times cited : (80)

References (74)
  • 7
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    • For other azametallacyclopentadienes of group 4 metals, see: Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058.
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    • This suggests the importance of the presence of a coordinating moiety in the nitrile. See ref 8 and the following: Bertus, P.; Szymoniak, J. J. Org. Chem. 2002, 67, 3965-3968.
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  • 13
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    • Nonetheless, since α-oxynitriles and their derivatives are readily obtained by the cyanohydrin synthesis and its modifications, this reaction will find reasonable application. See: North, N., Ed. Tetrahedron (Symposium-in-Print) 2004, 60, 10385-10568.
    • (2004) Tetrahedron (Symposium-in-Print) , vol.60 , pp. 10385-10568
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  • 18
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    • (d) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 12, pp 741-770.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 741-770
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    • (f) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.: Pergamon Press: Oxford, U.K., 1991; Vol. 5, pp 1129-1162.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 1129-1162
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  • 29
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    • (b) Wakatsuki, Y.; Yamazaki, H. J. Chem. Soc., Dalton Trans. 1978, 1278-1282. There had been no reports on the selective cyclotrimerization of two different unsymmetrical acetylenes and a nitrile, before we and others reported such examples (see refs 8 and 9).
    • (1978) J. Chem. Soc., Dalton Trans. , pp. 1278-1282
    • Wakatsuki, Y.1    Yamazaki, H.2
  • 30
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    • For recent reports, which deal with the cyclotrimerization of the same (refs 7c-j), symmetrical (ref 7k), or tethered (refs 71-r) substrates, see: (c) Bianchini, C.; Meli, A.; Peruzzini, M.; Vacca, A.; Vizza, F. Organometallics 1991, 10, 645-651.
    • (1991) Organometallics , vol.10 , pp. 645-651
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  • 46
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    • Suzuki, D.; Tanaka, R.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2002, 124, 3518-3519. This reaction has the following feature: (i) single pyridines were obtained, for the first time, from two different, unsymmetrical acetylenes and a nitrile, and (ii) titanated pyridines were produced rather than pyridines themselves.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 3518-3519
    • Suzuki, D.1    Tanaka, R.2    Urabe, H.3    Sato, F.4
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    • note
    • This is commercially available.
  • 50
    • 19744364646 scopus 로고    scopus 로고
    • note
    • The intermediates 16a,b correspond to the [4 + 2]-type and insertion mechanisms, respectively. See: ref 10.
  • 52
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    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K.
    • Ferreri, C.; Palumbo, G.; Caputo, R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 1, pp 139-172.
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    • Ferreri, C.1    Palumbo, G.2    Caputo, R.3
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    • Reetz, M. T. In Organometallics in Synthesis; Schlosser, M., Ed.; Wiley: Chichester, U.K., 1994; pp 195-282.
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  • 58
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    • note
    • Pyridine 45 was previously prepared in 10 steps, in 8% overall yield, and as 96% ee from 1,1-dimethoxy-2-propanone. See: ref 14.
  • 61
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    • Intermolecular double addition of acetylene-group 4 metal complexes to electrophilic carbon-heteroatom multiple bonds such as aldehydes, ketones, and imines is quite rare and is so far limited to a reactive acetylene complex such as that derived from enyne or an active electrophile represented by carbon dioxide: Hamada, T.; Mizojiri, R.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2000, 122, 7138-7139.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 7138-7139
    • Hamada, T.1    Mizojiri, R.2    Urabe, H.3    Sato, F.4
  • 63
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    • Six, Y. Eur. J. Org. Chem. 2003, 1157-1171. To the contrary, the selective monoaddition of acetylene-group 4 metal complexes to these compounds is well-documented in the following reviews. See: refs 1-3.
    • (2003) Eur. J. Org. Chem. , pp. 1157-1171
    • Six, Y.1
  • 66
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    • To our best knowledge, the double addition of acetylene-group 4 metal complexes to nitriles has not been reported (see ref 3). A relevant double addition of a titanacycle to nitriles was only reported for titanacyclobutenes, yielding pyridines after aqueous workup: Doxsee, K. M.; Mouser, J. K. M. Organometallics 1990, 9, 3012-3014.
    • (1990) Organometallics , vol.9 , pp. 3012-3014
    • Doxsee, K.M.1    Mouser, J.K.M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.