Le palladium, un catalyseur magique au service des chimistes

Jean-Pierre Genet

doi:10.1051/medsci/201026121095

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Volume 26 / Numéro 12 (Décembre 2010)

Med Sci (Paris), 26 12 (2010) 1095-1098

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Numéro		Med Sci (Paris) Volume 26, Numéro 12, Décembre 2010


Page(s)		1095 - 1098
Section		Repères
DOI		https://doi.org/10.1051/medsci/201026121095
Publié en ligne		15 décembre 2010

Heck RF. Acylation, methylation, and carboxyalkylation of olefins by Group VIII metal derivatives. J Am Chem Soc 1968 ; 90 : 5518-26. [Google Scholar]
Heck RF, Nolley JP. Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides. J Org Chem Soc 1972 ; 37 : 2320-2. [Google Scholar]
Mizoroki T, Mori K, Ozaki O. Arylation of olefin with iodobenzene catalyzed by Palladium. Bull Chem Soc Jpn 1973 ; 46 : 1505-8. [Google Scholar]
Heck RF. Palladium-catalyzed reactions of organic halides with olefins. Acc Chem Res 1979 ; 12 : 146-51. [Google Scholar]
Brase S, De Meijere A, Dyker G, et al. Handbook of organopalladium chemistry for organic synthesis. Chapters IV, IV.1, IV1.2, IV.2.2., IV.2. In : Negishi E, ed. New York : John Wiley and Sons Inc, 2002 : 1123-315. [Google Scholar]
Negishi E, King AO, Okukado N. Selective carbon-carbon bond formation via transition metal catalysis. A highly selective synthesis of unsymmetrical biaryls and diarylmethanes by the Nickel- or Palladium-catalyzed reaction of aryl- and benzylzinc derivatives with aryl halides. J Org Chem 1977 ; 42 : 1821-3. [Google Scholar]
Negishi E. Controlled carbometalation as a new tool for carbon-carbon bond formation and its application to cyclization. Acc Chem Res 1987 ; 20 : 65-72. [Google Scholar]
Negishi E, Hu Q, Huang Z, et al. Pd-Catalyzed alkenylation by the Negishi coupling. Aldrichimica Acta 2005 ; 38 : 71-86. [Google Scholar]
Negishi E, Anastasia L. Palladium-catalyzed alkynylation. Chem Rev 2003 ; 103 : 1979-2017. [Google Scholar]
Negishi, E, Wang Rao Xu Z. Alkyne elementometalation-Pd-catalyzed cross- coupling. Toward synthesis of all conceivable types of acyclic alkenes in high yields, efficiently, selectively, economically, and safely: green way. J Org Chem 2010 ; 75 : 3151-82. [Google Scholar]
Miyaura N, Yamada K, Suzuki A. A new stereospecific cross-coupling by the Palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or l-alkynyls halides. Tetrahedron Letters 1979 ; 36 : 3437-40. [Google Scholar]
Miyaura N, Yamada K, Suginome H, Suzuki A. Novel and convenient method for the stereo- and regiospecific synthesis of conjugated alkadienes and alkenynes via the Palladium-catalyzed cross-coupling reaction of 1-alkenylboranes with bromoalkenes and bromoalkynes. J Am Chem Soc 1985 ; 107 : 972-80. [Google Scholar]
Miyaura N, Suzuki A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem Rev 1995 ; 95 : 2457-83. [Google Scholar]
Suzuki A. Overview of the Suzuki protocol with Boron. Handbook of organopalladium chemistry for organic synthesis. Chap. III.2.2. In : Negishi E, ed. New York : John Wiley and Sons Inc, 2002 : 249-62. [Google Scholar]
Buchwald SL (ed). Cross-coupling. Acc Chem Res 2008 ; 41 (n° spécial) : 1439-564. [Google Scholar]
Ishiyama T, Takagi J, Ishida K, et al. Mild iridium-catalyzed borylation of arenes. high turnover numbers, room temperature reactions, and isolation of a potential intermediate. J Am Chem Soc 2002 ; 124 : 390-1. [Google Scholar]
Darses S, Genet JP. Potassium organotrifluoroborates: new perspectives in organic synthesis. Chem Rev 2008 ; 108 : 288-325. [Google Scholar]
Nicolaou KC, Bulger PG, Sarlah D. Palladium-catalyzed cross-coupling reactions in total synthesis. Angew Chem Int Ed 2005 ; 44 : 4442-89. [Google Scholar]

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[1] Heck RF. Acylation, methylation, and carboxyalkylation of olefins by Group VIII metal derivatives. J Am Chem Soc 1968 ; 90 : 5518-26. [Google Scholar]

[2] Heck RF, Nolley JP. Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides. J Org Chem Soc 1972 ; 37 : 2320-2. [Google Scholar]

[3] Mizoroki T, Mori K, Ozaki O. Arylation of olefin with iodobenzene catalyzed by Palladium. Bull Chem Soc Jpn 1973 ; 46 : 1505-8. [Google Scholar]

[4] Heck RF. Palladium-catalyzed reactions of organic halides with olefins. Acc Chem Res 1979 ; 12 : 146-51. [Google Scholar]

[5] Brase S, De Meijere A, Dyker G, et al. Handbook of organopalladium chemistry for organic synthesis. Chapters IV, IV.1, IV1.2, IV.2.2., IV.2. In : Negishi E, ed. New York : John Wiley and Sons Inc, 2002 : 1123-315. [Google Scholar]

[6] Negishi E, King AO, Okukado N. Selective carbon-carbon bond formation via transition metal catalysis. A highly selective synthesis of unsymmetrical biaryls and diarylmethanes by the Nickel- or Palladium-catalyzed reaction of aryl- and benzylzinc derivatives with aryl halides. J Org Chem 1977 ; 42 : 1821-3. [Google Scholar]

[7] Negishi E. Controlled carbometalation as a new tool for carbon-carbon bond formation and its application to cyclization. Acc Chem Res 1987 ; 20 : 65-72. [Google Scholar]

[8] Negishi E, Hu Q, Huang Z, et al. Pd-Catalyzed alkenylation by the Negishi coupling. Aldrichimica Acta 2005 ; 38 : 71-86. [Google Scholar]

[9] Negishi E, Anastasia L. Palladium-catalyzed alkynylation. Chem Rev 2003 ; 103 : 1979-2017. [Google Scholar]

[10] Negishi, E, Wang Rao Xu Z. Alkyne elementometalation-Pd-catalyzed cross- coupling. Toward synthesis of all conceivable types of acyclic alkenes in high yields, efficiently, selectively, economically, and safely: green way. J Org Chem 2010 ; 75 : 3151-82. [Google Scholar]

[11] Miyaura N, Yamada K, Suzuki A. A new stereospecific cross-coupling by the Palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or l-alkynyls halides. Tetrahedron Letters 1979 ; 36 : 3437-40. [Google Scholar]

[12] Miyaura N, Yamada K, Suginome H, Suzuki A. Novel and convenient method for the stereo- and regiospecific synthesis of conjugated alkadienes and alkenynes via the Palladium-catalyzed cross-coupling reaction of 1-alkenylboranes with bromoalkenes and bromoalkynes. J Am Chem Soc 1985 ; 107 : 972-80. [Google Scholar]

[13] Miyaura N, Suzuki A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem Rev 1995 ; 95 : 2457-83. [Google Scholar]

[14] Suzuki A. Overview of the Suzuki protocol with Boron. Handbook of organopalladium chemistry for organic synthesis. Chap. III.2.2. In : Negishi E, ed. New York : John Wiley and Sons Inc, 2002 : 249-62. [Google Scholar]

[15] Buchwald SL (ed). Cross-coupling. Acc Chem Res 2008 ; 41 (n° spécial) : 1439-564. [Google Scholar]

[16] Ishiyama T, Takagi J, Ishida K, et al. Mild iridium-catalyzed borylation of arenes. high turnover numbers, room temperature reactions, and isolation of a potential intermediate. J Am Chem Soc 2002 ; 124 : 390-1. [Google Scholar]

[17] Darses S, Genet JP. Potassium organotrifluoroborates: new perspectives in organic synthesis. Chem Rev 2008 ; 108 : 288-325. [Google Scholar]

[18] Nicolaou KC, Bulger PG, Sarlah D. Palladium-catalyzed cross-coupling reactions in total synthesis. Angew Chem Int Ed 2005 ; 44 : 4442-89. [Google Scholar]