Heck Reaction

 

Definition:

Palladium-catalyzed carbon-carbon bond coupling of an alkyl, aryl or vinyl entity to an alkene.

 

Frequency of appearance:

        This bar graph represents all of the online articles that were found to contain this specific name reaction in the title of the article. Tetrahedron letters, Tetrahedron, Synthetic letters, Synthesis, Journal of Organic Chemistry and Journal of the American Chemical Society are represented here. This table by no means represents the periodicity of the name reaction found in the literature.

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Original Reference:

  1. R. F. Heck, J. P. Nolley, Jr., J. Org. Chem. 37, 2320 (1972).
  2. Heck, R.F., et al., J. Org. Chem., 1977, 42, 3903.

 

Recent academic references: Click here for more references

 

  1. Cobalt-Catalyzed Heck-Type Reaction of Alkyl Halides with Styrenes
  • Ikeda, Y.; Nakamura, T.; Yorimitsu, H.; Oshima, K.;
    J. Am. Chem. Soc.; 2002; 124(23); 6514-6515.      
  1. A Highly Efficient Palladium/Imidazolium Salt System for Catalytic Heck Reactions
  • Yang, Chuluo; Nolan, Steven P. Synlett; 10, 2001
  1. Synthesis of hydrazulenes via Zr-promoted bicylization of enynes and transition metal-catalyzed or radical cyclization of alkenyl iodides. Efficient synthesis of (_+)-7-epi-b-bulnesene.
  • Negishi, E.,* Ma, S.; Sugihara, T.; Noda, Y. J. Org. Chem., 1997, 62, 1922-1923.

                

  1. http://www.arkat-usa.org/ark/journal/2002/General/1_319D/319.pdf

 

Recent process references:

  1. A Reliable Multikilogram-Scale Synthesis of 2-Acetamido-5-Vinylpyridine Using Catalytic BINAP in a Modified Heck Reaction
  • Raggon, J. W.; Snyder, W. M.; Org. Process Res. Dev.; 2002; 6(1); 67-69.  
  1. Optimisation of Palladium-Based Supported Liquid-Phase Catalysts in the Heck Reaction
  • Mirza, A. R.; Anson, M. S.; Hellgardt, K.; Leese, M. P.; Thompson, D. F.; Tonks, L.; Williams, J. M. J.;
    Org. Process Res. Dev.; 1998; 2(5); 325-331.  
  1. A Scalable Synthesis of the Thromboxane Receptor Antagonist 3-{3-[2-(4-Chlorobenzenesulfonamido)ethyl]-5-(4-fluorobenzyl)phenyl}propionic Acid via a Regioselective Heck Cross-Coupling Strategy
  • Waite, D. C.; Mason, C. P.; Org. Process Res. Dev.; 1998; 2(2); 116-120.  

 

Mechanism:

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Scope and Limitations:

 

Synonyms:

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