Yu, J.-Q.: 2016 Science of Synthesis, 3a: Catalytic Transformations via C—H Activation 1 DOI: 10.1055/sos-SD-217-00003
Catalytic Transformations via C—H Activation 1

1.1 C—C Bond Formation by Arene C—H Activation

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Book

Editor: Yu, J.-Q.

Authors: Carreira, E. M.; Decicco, C. P.; Fuerstner, A.; Koch, G.; Molander, G. A.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Title: Catalytic Transformations via C—H Activation 1

Subtitle: C-C, C-N, C-O, C-Hal, and C-B Bond Formation

Print ISBN: 9783131711311; Online ISBN: 9783132403413; Book DOI: 10.1055/b-003-129295

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

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Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Type: Multivolume Edition

 


Abstract

The palladium(0)-catalyzed C—H arylation reaction is one of the pioneering transformations in C—H activation chemistry in general. In the past two decades, the method has been extensively developed and now represents a very powerful tool for the construction of C(sp2)—C(sp2) bonds. In this chapter, the palladium(0)-catalyzed C—H arylation of aromatic compounds is reviewed. The application of the method toward the synthesis of polycyclic aromatic hydrocarbons (PAHs), a variety of biaryl compounds, and natural products, with emphasis on the most practical and efficient protocols, are discussed.

 
  • 24 Campeau L.-C, Fagnou K. Chem. Commun. (Cambridge) 2006; 1253
  • 29 Negishi E.-i. Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley; New York 2002
  • 51 Yranzo GI, Elguero J, Flammang R, Wentrup C. Eur. J. Org. Chem. 2001; 2209
  • 53 de Frutos Ó, Gómez-Lor B, Granier T, Monge MÁ, Gutiérrez-Puebla E, Echavarren AM. Angew. Chem. Int. Ed. 1999; 38: 204
  • 58 Gómez-Lor B, de Frutos Ó, Echavarren AM, Gómez-Lor B. Chem. Commun. (Cambridge) 1999; 2431
  • 59 Paul S, Jana R, Ray JK. Synlett 2010; 1463
  • 61 Smet M, Van Dijk J, Dehaen W. Synlett 1999; 495
  • 71 Bringmann G, Keller PA, Rölfing K. Synlett 1994; 423
  • 79 Lafrance M, Blaquiere N, Fagnou K. Eur. J. Org. Chem. 2007; 811
  • 80 Lafrance M, Blaquiere N, Fagnou K. Chem. Commun. (Cambridge) 2004; 2874
  • 84 Ames DE, Opalko A. Synthesis 1983; 234
  • 98 Bedford RB, Cazin CSJ. Chem. Commun. (Cambridge) 2002; 2310
  • 101 Iwaki T, Yasuhara A, Sakamoto T. J. Chem. Soc., Perkin Trans. 1 1999; 1505
  • 107 Marquise N, Harford PJ, Chevallier F, Roisnel T, Wheatley AEH, Gros PC, Mongin F. Tetrahedron Lett. 2013; 54: 3154
  • 115 Majumdar KC, Taher A, Debnath P. Synthesis 2009; 793
  • 121 Wu J, Nie L, Luo J, Dai W.-M. Synlett 2007; 2728
  • 122 Harayama T, Sato T, Hori A, Abe H, Takeuchi Y. Synlett 2003; 1141
  • 123 Harayama T, Sato T, Hori A, Abe H, Takeuchi Y. Synthesis 2004; 1446
  • 125 Herrmann WA, Brossmer C, Öfele K, Reisinger C.-P, Priermeier T, Beller M, Fischer H. Angew. Chem. Int. Ed. Engl. 1995; 34: 1844
  • 126 Dyker G, Borowski S, Heiermann J, Körning J, Opwis K, Henkel G, Köckerling M. J. Organomet. Chem. 2000; 606: 108
  • 128 Miura M, Pivsa-Art S, Satoh T, Nomura M, Miura M, Dyker G, Heiermann J. Chem. Commun. (Cambridge) 1998; 1889
  • 138 Satoh T, Inoh J.-i, Kawamura Y, Kawamura Y, Miura M, Nomura M. Bull. Chem. Soc. Jpn. 1998; 71: 2239