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Volumn 11, Issue 3, 2009, Pages 689-692

Amide-directed alkenylation of sp2 C-H bonds catalyzed by a cationic Rh(I)/BIPHEP complex under mild conditions: Dramatic rate acceleration by a 1-pyrrolidinecarbonyl group

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EID: 62149126540     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802767s     Document Type: Article
Times cited : (88)

References (50)
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    • The reaction of phenyl-substituted alkenylamide 1k with 2a proceeded at 80 °C in quantitative yield, while the stereochemistry of the product 3ka has not been determined. (Chemical Equation Presented)
    • The reaction of phenyl-substituted alkenylamide 1k with 2a proceeded at 80 °C in quantitative yield, while the stereochemistry of the product 3ka has not been determined. (Chemical Equation Presented)
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    • During preparation of this manuscript, ketone carbonyl-directed alkenylations and alkylations of aryl ketones with diphenylacetylene, styrene, and norbornene catalyzed by cationic Ir(I)/biaryldiphosphine complexes were reported; see: (a) Tsuchikama, K.; Kasagawa, M.; Hashimoto, Y-k.; Endo, K.; Shibata, T. J. Organomet. Chem. 2008, 693, 3939. Amide carbonyl-directed asymmetric alkylations of a NH2-benzamide with norbornene catalyzed by a Ir(I)/bisphosphine/Cp complex were reported; see:
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    • 2 C-H bonds with alkynes have been developed by using various transition-metal complexes; see: (a) Aubert, C.; Betschmann, P.; Eichberg, M. J.; Gandon, V.; Heckrodt, T. J.; Lehmann, J.; Malacria, M.; Masjost, B.; Paredes, E.; Vollhardt, K. P. C.; Whitener, G. D. Chem.-Eur. J. 2007, 13, 7443.
    • 2 C-H bonds with alkynes have been developed by using various transition-metal complexes; see: (a) Aubert, C.; Betschmann, P.; Eichberg, M. J.; Gandon, V.; Heckrodt, T. J.; Lehmann, J.; Malacria, M.; Masjost, B.; Paredes, E.; Vollhardt, K. P. C.; Whitener, G. D. Chem.-Eur. J. 2007, 13, 7443.
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    • The reaction of alkenylamide 1c with 1,6-diyne 9 also proceeded in high yield, while the stereochemistry of the product 11 has not been determined. (Chemical Equation Presented)
    • The reaction of alkenylamide 1c with 1,6-diyne 9 also proceeded in high yield, while the stereochemistry of the product 11 has not been determined. (Chemical Equation Presented)


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