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Volumn 111, Issue 3, 2011, Pages 1170-1214

Intermolecular dehydrogenative heck reactions

Author keywords

[No Author keywords available]

Indexed keywords

ACETATE LIGANDS; C-C BONDS; C-H BOND; ETHYL ACRYLATES; HECK REACTIONS; IN-SITU FORMATIONS; MIZOROKI-HECK REACTION; REACTION CONDITIONS; ROOM TEMPERATURE; SOLVENT MIXTURES;

EID: 79952677383     PISSN: 00092665     EISSN: 15206890     Source Type: Journal    
DOI: 10.1021/cr100209d     Document Type: Review
Times cited : (955)

References (318)
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    • The 3-arylacrylate shown in eq 9 has also been obtained from treatment of the σ-palladium complex of the naphthalenic substrate with ethyl acrylate. (39)
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    • A footnote in Kasahara's paper mentions a communication on such a reaction from Fujiwara's team at the 26th Annual Meeting of the Chemical Society of Japan (1972)
    • A footnote in Kasahara's paper mentions a communication on such a reaction from Fujiwara's team at the 26th Annual Meeting of the Chemical Society of Japan (1972).
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    • The yields of the disubstituted BQs indicated in refs 45 and 98 are inverted.
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    • In contrast, the enantioselective intramolecular DHR has been recently documented. (20)
    • In contrast, the enantioselective intramolecular DHR has been recently documented. (20)
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    • 2 contrasts with the results with oxygen as the reoxidant. (96)
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    • For reviews on high-oxidation-state palladium catalysis in the presence of hypervalent iodine reagents, see ref 70a.
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    • For the proposal of this term for such reactions, see;;;;;, For recent reviews concerning reactions in water, on water, and by water, see; Org. Biomol. Chem. 2010, 8, 4043
    • For the proposal of this term for such reactions, see Narayan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolb, H. C.; Sharpless, K. B. Angew. Chem., Int. Ed. 2005, 44, 3275 For recent reviews concerning reactions in water, on water, and by water, see Mase, N.; Barbas, C. F. Org. Biomol. Chem. 2010, 8, 4043
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    • 2 (as wrote in the legend of Table 1) was used as the initial catalyst, but both the supplementary information of this paper and a subsequent account (;;;; Synlett 2006, 3382) indicate the use of the former
    • 2 (as wrote in the legend of Table 1) was used as the initial catalyst, but both the supplementary information of this paper and a subsequent account (Daugulis, O.; Zaitsev, V. G.; Shabashov, D.; Pham, Q.-N.; Lazareva, A. Synlett 2006, 3382) indicate the use of the former.
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    • According to Zaitsev and Daugulis, (142) the order of reactivity of halide olefins (Br > I > Cl) excludes a mechanism involving an electrophilic attack on the Pd-C bond or a Pd(IV) intermediate. For such possibilities, see
    • According to Zaitsev and Daugulis, (142) the order of reactivity of halide olefins (Br > I > Cl) excludes a mechanism involving an electrophilic attack on the Pd-C bond or a Pd(IV) intermediate. For such possibilities, see Tremont, S. J.; Rahman, H. J. Am. Chem. Soc. 1984, 106, 5759
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    • For such a selective substitution, see Rauf, W.; Brown, J. M. Synlett 2009, 3103
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    • Another possibility would be a Fujiwara-type substitution followed by hydroamination
    • Another possibility would be a Fujiwara-type substitution followed by hydroamination.
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    • 2 directly bounded to palladium has been suggested for the ortho-palladation of N-benzylidenebenzenamine
    • 2 directly bounded to palladium has been suggested for the ortho-palladation of N-benzylidenebenzenamine: Gomez, M.; Granell, J.; Martinez, M. J. Chem. Soc., Dalton Trans. 1998, 37
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    • 3 = Et and Y = CH=CH. (167)
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    • Acidic conditions are required to regenerate Pd(II) from Pd(0) with benzoquinone: ref 136a
    • Acidic conditions are required to regenerate Pd(II) from Pd(0) with benzoquinone: ref 136a.
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    • Under particular conditions, such regeneration has however occurred in the absence of protic acid
    • Under particular conditions, such regeneration has however occurred in the absence of protic acid: Babjak, M.; Zálupský, P.; Gracza, T. Arkivoc 2005, v, 45
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    • Compared to 25E, the formation of a four-membered palladacycle would be disfavored
    • Compared to 25E, the formation of a four-membered palladacycle would be disfavored.
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    • The regioselectivity of the Pd-catalyzed arylation of indoles is also dependent on the experimental conditions and substrate substitution. For reviews, see
    • The regioselectivity of the Pd-catalyzed arylation of indoles is also dependent on the experimental conditions and substrate substitution. For reviews, see Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174
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    • For the reoxidation of palladium with 1,2,4-trichlorobenzene, see; Ger. Offen. DE 4,415,803
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    • The electrophilic substitution of indoles has a strong preference for the C3 position: Jackson, A. H.; Lynch, P. P. J. Chem. Soc., Perkin Trans. 2 1987, 1483 and cited references
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    • A similar mechanism, supported with kinetic isotope effect studies, has been assumed for the Heck reaction of aryl iodides with indoles
    • A similar mechanism, supported with kinetic isotope effect studies, has been assumed for the Heck reaction of aryl iodides with indoles. Lane, B. S.; Brown, M. A.; Sames, D. J. Am. Chem. Soc. 2005, 127, 8050
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    • Pd-catalyzed allylations of indoles and pyrroles using allylic alcohols instead of allylic acetates have also been reported, but they occur under Pd(0) catalysis and, therefore, are out of the scope of the present review. For these allylations, see
    • Pd-catalyzed allylations of indoles and pyrroles using allylic alcohols instead of allylic acetates have also been reported, but they occur under Pd(0) catalysis and, therefore, are out of the scope of the present review. For these allylations, see Billups, W. E.; Erkes, R. S.; Reed, L. E. Synth. Commun. 1980, 10, 147
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    • Given a referee remark, the direction of the arrows indicating the displacement of electrons for the rearrangement of 29C is opposite to that of the published report
    • Given a referee remark, the direction of the arrows indicating the displacement of electrons for the rearrangement of 29C is opposite to that of the published report.
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    • A referee suggested that electronic factors could be involved in this selectivity switch
    • A referee suggested that electronic factors could be involved in this selectivity switch.
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    • For interesting reports concerning the formation of ArPd(II) intermediates from the reaction of Pd(II) species with ArH, see
    • For interesting reports concerning the formation of ArPd(II) intermediates from the reaction of Pd(II) species with ArH, see García-Cuadrado, D.; de Mendoza, P.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2007, 129, 6880
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    • García-Cuadrado, D.1    De Mendoza, P.2    Braga, A.A.C.3    Maseras, F.4    Echavarren, A.M.5
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    • Poor reactivity of indoles and pyridines was observed under these conditions. (199)
    • Poor reactivity of indoles and pyridines was observed under these conditions. (199)


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