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Volumn 13, Issue 9, 2011, Pages 2452-2455

Fluorenone synthesis by palladacycle-catalyzed sequential reactions of 2-bromobenzaldehydes with arylboronic acids

Author keywords

[No Author keywords available]

Indexed keywords

BENZALDEHYDE DERIVATIVE; BORONIC ACID DERIVATIVE; BROMINE DERIVATIVE; FLUORENE; FLUORENE DERIVATIVE; PALLADIUM;

EID: 79955641668     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200693d     Document Type: Article
Times cited : (58)

References (73)
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    • Most type I palladacycles are known to exist as bridged dimers and to dissociate into monomeric forms during reactions. Type I palladacycles in this paper were drawn in monomeric forms.
    • Most type I palladacycles are known to exist as bridged dimers and to dissociate into monomeric forms during reactions. Type I palladacycles in this paper were drawn in monomeric forms.
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    • For recent reviews on transition metal-catalyzed addition reactions of organoborons with carbonyl-containing compounds, see
    • For recent reviews on transition metal-catalyzed addition reactions of organoborons with carbonyl-containing compounds, see: Miyaura, N. Synlett 2009, 2039-2050
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    • references cited therein
    • Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169-196 and references cited therein
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    • Fagnou, K.1    Lautens, M.2
  • 33
    • 33746597447 scopus 로고    scopus 로고
    • For recent examples of Pd(II)-catalyzed oxidation of alcohols, see
    • For recent examples of Pd(II)-catalyzed oxidation of alcohols, see: R., J.; Goddard, W. A., III J. Am. Chem. Soc. 2006, 128, 9651-9660
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 9651-9660
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    • For recent examples of other tandem, domino, sequential, or one-pot reaction approach to fluorenones, see
    • For recent examples of other tandem, domino, sequential, or one-pot reaction approach to fluorenones, see: Sun, C.-L.; Liu, N.; Li, B.-J.; Yu, D.-G.; Wang, Y.; Shi, Z.-J. Org. Lett. 2010, 12, 184-187
    • (2010) Org. Lett. , vol.12 , pp. 184-187
    • Sun, C.-L.1    Liu, N.2    Li, B.-J.3    Yu, D.-G.4    Wang, Y.5    Shi, Z.-J.6
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    • The use of 6 equiv of base was necessary for the first step addition reaction to complete without the occurrence of the cross-coupling reaction.
    • The use of 6 equiv of base was necessary for the first step addition reaction to complete without the occurrence of the cross-coupling reaction.
  • 64
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    • Fluorenol was observed as the intermediate (GC-MS analysis) when the reaction was stopped after 2 h.
    • Fluorenol was observed as the intermediate (GC-MS analysis) when the reaction was stopped after 2 h.


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