PDF herunterladen
Yu, J.-Q.: 2016 Science of Synthesis, 3a: Catalytic Transformations via C—H Activation 1 DOI: 10.1055/sos-SD-217-00035
Catalytic Transformations via C—H Activation 1

1.1.3 Arylation Using a Palladium(II) Catalyst

Weitere Informationen

Buch

Herausgeber: Yu, J.-Q.

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

Titel: Catalytic Transformations via C—H Activation 1

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

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

1st edition © 2016 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Fachgebiete: Organische Chemie;Chemische Reaktionen, Katalyse;Organometallchemie;Chemische Labormethoden, Stöchiometrie

Science of Synthesis Reference Libraries



Übergeordnete Publikation

Titel: Science of Synthesis

DOI: 10.1055/b-00000101

Typ: Mehrbändiges Werk

Auch verfügbar auf
 


Abstract

This chapter focuses on the synthesis of biaryl C—C bonds via palladium(II)-catalyzed direct arylation of arenes with aryltin, arylboron, and arylsilicon reagents and aromatic carboxylic acids. Due to the ubiquity of C—H bonds in organic molecules, these methods represent an efficient and straightforward approach to biaryl C—C bonds. The chapter is organized based on the type of arylating reagent used.

Schlüsselwörter

C—H activation - arenes - arylation - biaryls - cross-coupling reactions - carboxylic acids - organometallic reagents - palladium catalysis
 
  • 1 Chen X, Li J.-J, Hao X.-S, Goodhue CE, Yu J.-Q. J. Am. Chem. Soc. 2006; 128: 78
  • 2 Chen X, Goodhue CE, Yu J.-Q. J. Am. Chem. Soc. 2006; 128: 12634
  • 3 Li B.-J, Yang S.-D, Shi Z.-J. Synlett 2008; 949
  • 4 Ackermann L, Vicente R, Kapdi AR. Angew. Chem. Int. Ed. 2009; 48: 9792
  • 5 Chen X, Engle KM, Wang D.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
  • 6 Sun C.-L, Li B.-J, Shi Z.-J. Chem. Commun. (Cambridge) 2010; 46: 677
  • 7 Shi W, Liu C, Lei A. Chem. Soc. Rev. 2011; 40: 2761
  • 8 Kakiuchi F, Kan S, Igi K, Chatani N, Murai S. J. Am. Chem. Soc. 2003; 125: 1698
  • 9 Kakiuchi F, Matsuura Y, Kan S, Chatani N. J. Am. Chem. Soc. 2005; 127: 5936
  • 10 Gooßen LJ, Rodríguez N, Gooßen K. Angew. Chem. Int. Ed. 2008; 47: 3100
  • 11 Cornella J, Larrosa I. Synthesis 2012; 44: 653
  • 12 Kawai H, Kobayashi Y, Oi S, Inoue Y. Chem. Commun. (Cambridge) 2008; 1464
  • 13 Xue D, Li J, Liu Y.-X, Han W.-Y, Zhang Z.-T, Wang C, Xiao J. Synlett 2012; 23: 1941
  • 14 Giri R, Maugel N, Li J.-J, Wang D.-H, Breazzano SP, Saunders LB, Yu J.-Q. J. Am. Chem. Soc. 2007; 129: 3510
  • 15 Wang D.-H, Mei T.-S, Yu J.-Q. J. Am. Chem. Soc. 2008; 130: 17676
  • 16 Engle KM, Thuy-Boun PS, Dang M, Yu J.-Q. J. Am. Chem. Soc. 2011; 133: 18183
  • 17 Gao D.-W, Shi Y.-C, Gu Q, Zhao Z.-L, You S.-L. J. Am. Chem. Soc. 2013; 135: 86
  • 18 Shi Z, Li B, Wan X, Cheng J, Fang Z, Cao B, Qin C, Wang Y. Angew. Chem. Int. Ed. 2007; 46: 5554
  • 19 Sun C.-L, Liu N, Li B.-J, Yu D.-G, Wang Y, Shi Z.-J. Org. Lett. 2009; 12: 184
  • 20 Kirchberg S, Vogler T, Studer A. Synlett 2008; 2841
  • 21 Chu J.-H, Tsai S.-L, Wu M.-J. Synthesis 2009; 3757
  • 22 Romero-Revilla JA, García-Rubia A, Goméz Arrayás R, Fernández-Ibáñez MÁ, Carretero JC. J. Org. Chem. 2011; 76: 9525
  • 23 Nishikata T, Abela AR, Huang S, Lipshutz BH. J. Am. Chem. Soc. 2010; 132: 4978
  • 24 Yang S.-D, Sun C.-L, Fang Z, Li B.-J, Li Y.-Z, Shi Z.-J. Angew. Chem. Int. Ed. 2008; 47: 1473
  • 25 Wei Y, Kan J, Wang M, Su W, Hong M. Org. Lett. 2009; 11: 3346
  • 26 Yang S, Li B, Wan X, Shi Z. J. Am. Chem. Soc. 2007; 129: 6066
  • 27 Li W, Yin Z, Jiang X, Sun P. J. Org. Chem. 2011; 76: 8543
  • 28 Funaki K, Kawai H, Sato T, Oi S. Chem. Lett. 2011; 40: 1050
  • 29 Voutchkova A, Coplin A, Leadbeater NE, Crabtree RH. Chem. Commun. (Cambridge) 2008; 6312
  • 30 Wang C, Piel I, Glorius F. J. Am. Chem. Soc. 2009; 131: 4194
  • 31 Xie K, Yang Z, Zhou X, Li X, Wang S, Tan Z, An X, Guo C.-C. Org. Lett. 2010; 12: 1564
  • 32 Zhao H, Wei Y, Xu J, Kan J, Su W, Hong M. J. Org. Chem. 2011; 76: 882