Ligand-switchable directing effects of tethered alkenes in nickel-catalyzed additions to alkynes

Journal of the American Chemical Society

Volumn 126, Issue 47, 2004, Pages 15342-15343

  Miller, Karen M ^a   Jamison, Timothy F ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; ALLYL COMPOUND; LIGAND; NICKEL;

ADDITION REACTION; ARTICLE; BIOTRANSFORMATION; CATALYSIS; CATALYST; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STOICHIOMETRY;

EID: 9644260362     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0446799     Document Type: Article

References (29)

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3. Other examples of catalytic reductive coupling reactions of 1,3-enynes and aldehydes: (a) (Ni) Mahandru, G. M.; Liu, G.; Montgomery, J. J. Am. Chem. Soc. 2004, 126, 3698-3699. (b) (Rh) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4664-4668.
4. Other examples of catalytic reductive coupling reactions of 1,3-enynes and aldehydes: (a) (Ni) Mahandru, G. M.; Liu, G.; Montgomery, J. J. Am. Chem. Soc. 2004, 126, 3698-3699. (b) (Rh) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4664-4668.
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7. Reviews of catalytic reductive coupling reactions: (a) Miller, K. M.; Molinaro, C.; Jamison, T. F. Tetrahedron: Asymmetry 2003, 14, 3619-3625. (b) Ikeda, S.-i. Angew. Chem., Int. Ed. 2003, 42, 5120-5122. (c) Jang, H.-Y.; Krische, M. J. Acc. Chem. Res. 2004, 37, 653-661. (d) Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890-3908.
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9. Aromatic aldehydes are of considerably reduced efficacy. An extended reaction time (40 h) was required for a 26% yield (>95:5 regioselectivity) in a coupling between 1 h and PhCHO. See Supporting Information.
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11. Details in Supporting Information.
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