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Volumn 74, Issue 9, 2009, Pages 3576-3578

Nickel- and rhodium-catalyzed addition of terminal silylacetylenes to propargyl amines: Catalyst-dependent complementary regioselectivity

Author keywords

[No Author keywords available]

Indexed keywords

CONTROLLED SWITCHING; PROPARGYL; RHODIUM CATALYSTS; RHODIUM-CATALYZED; STARTING MATERIALS;

EID: 66449112804     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900474d     Document Type: Article
Times cited : (25)

References (37)
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    • Pioneering work of nickel-catalyzed cross-dimerization between terminal and internal alkynes: (a) Ishikawa, M.; Ohshita, J.; Ito, Y.; Minato, A. J. Chem. Soc., Chem. Commun. 1988, 804. In recent years, Suginome reported nickel-catalyzed addition of triisopropylsilylacetylene to 1,3-dienes and styrenes.
    • Pioneering work of nickel-catalyzed cross-dimerization between terminal and internal alkynes: (a) Ishikawa, M.; Ohshita, J.; Ito, Y.; Minato, A. J. Chem. Soc., Chem. Commun. 1988, 804. In recent years, Suginome reported nickel-catalyzed addition of triisopropylsilylacetylene to 1,3-dienes and styrenes.
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    • Shirakura, M.; Suginome, M. Org. Lett. 2009, 11, 523. Nickel-catalyzed selective cross-trimerization: (d) Ogata, K.; Murayama, H.; Sugasawa, J.; Suzuki, N.; Fukuzawa, S. J. Am. Chem. Soc. 2009, 131, 3176.
    • (c) Shirakura, M.; Suginome, M. Org. Lett. 2009, 11, 523. Nickel-catalyzed selective cross-trimerization: (d) Ogata, K.; Murayama, H.; Sugasawa, J.; Suzuki, N.; Fukuzawa, S. J. Am. Chem. Soc. 2009, 131, 3176.
  • 33
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    • Katagiri, T.; Tsurugi, H.; Satoh, T.; Miura, M. Chem. Commun. 2008, 3405. See also: (d) Satoh, T.; Tsurugi, H.; Miura, M. Chem. Rec. 2008, 8, 326.
    • (c) Katagiri, T.; Tsurugi, H.; Satoh, T.; Miura, M. Chem. Commun. 2008, 3405. See also: (d) Satoh, T.; Tsurugi, H.; Miura, M. Chem. Rec. 2008, 8, 326.
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    • (2001)
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    • Unfortunately, the reaction with alkyl-substituted substrates such as diethyl(2-heptynyl)amine was unsuccessful. A large amount of the starting material was recovered intact.
    • Unfortunately, the reaction with alkyl-substituted substrates such as diethyl(2-heptynyl)amine was unsuccessful. A large amount of the starting material was recovered intact.


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