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Volumn , Issue 13, 2007, Pages 2029-2032

Rhodium-catalyzed arylative cyclization reaction of diynes with arylboronic acids

Author keywords

Addition reactions; Arylboronic acids; Cyclizations; Diynes; Rhodium

Indexed keywords

1,2 DIALKYLIDENECYCLOALKANE; ALKANE DERIVATIVE; ALKYNE DERIVATIVE; BENZENEBORONIC ACID; BORONIC ACID DERIVATIVE; MALONIC ACID; RHODIUM; UNCLASSIFIED DRUG;

EID: 34548152096     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-984879     Document Type: Article
Times cited : (21)

References (35)
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    • For a review on transition-metal-catalyzed carbocyclizations of diynes, see
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    • Borylstannanes: Onozawa, S.; Hatanaka, Y.; Choi, N.; Tanaka, M. Organometallics 1997, 16, 5389.
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    • Hydrogen equivalent: Trost, B. M.; Lee, D. C. J. Am. Chem. Soc. 1988, 110, 7255.
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    • Hydrocarboxylation: Kim, H.; Goble, S. D.; Lee, C. J. J. Am. Chem. Soc. 2007, 129, 1030.
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    • Phenylboroxine was used instead of phenylboronic acid to avoid proton scrambling
    • Phenylboroxine was used instead of phenylboronic acid to avoid proton scrambling.
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    • 4. The solvent was removed under reduced pressure and the residue was purified by preparative TLC (hexane-EtOAc) to give 3.
    • 4. The solvent was removed under reduced pressure and the residue was purified by preparative TLC (hexane-EtOAc) to give 3.
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    • For regioselectivities of transition-metal-catalyzed reactions of unsymmetrical 1,6-diynes, see: a
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    • A reaction using unsymmetrical 1,6-diyne disubstituted with methyl and phenyl groups (4, R = Ph) proceeded at 100°C to afford a complex mixture of products, although the reason is unclear.
    • A reaction using unsymmetrical 1,6-diyne disubstituted with methyl and phenyl groups (4, R = Ph) proceeded at 100°C to afford a complex mixture of products, although the reason is unclear.


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